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THE TRAUNER RESEARCH GROUP

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Denksport

Difficulty: 1 - 3, where 3 = most difficult
2024-03-13
Step count:
27
Difficulty:
3
Total Synthesis, Relay Synthesis, and Structural Confirmation of the C18-Norditerpenoid Alkaloid Neofinaconitine

Shi, Y.; Wilmot, J. T.; Nordstrøm, L. U.; Tan, D. S.; Gin, D. Y. J. Am. Chem. Soc. 2013, 135, 14313-14320

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2024-03-06
Step count:
17
Difficulty:
2
Diastereoselective Synthesis of trans-anti-Hydrophenanthrenes via Ti-mediated Radical Cyclization and Total Synthesis of Kamebanin.

Suzuki, T.; Ikeda, W.; Kanno, A.; Ikeuchi, K.; Tanino, K. Chem. Eur. J. 2023, 29, e202203511

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2024-02-28
Step count:
26
Difficulty:
2
Enantioselective Syntheses of Wickerols A and B

Chung, J; Capani, J. S; Göhl, M; Roosen, P. C; Vanderwal C. D. J. Am. Chem. Soc. 2023, 145, 6486–6497

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2024-02-21
Step count:
16
Difficulty:
3
Synthesis of Pleuromutilin

Foy, N. J.; Pronin S. V.; J. Am. Chem. Soc. 2022, 144, 10174–10179.

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2024-02-14
Step count:
17
Difficulty:
2
A Concise Total Synthesis of (+)-Waihoensene Guided by Quaternary Center Analysis

Peng, C.; Arya, P.; Zhou, Z.; Snyder, S. Angew. Chem. Int. Ed. 2020, 59, 13521 – 13525.

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2024-02-07
Step count:
13
Difficulty:
2
Catalysis-Enabled 13-Step Total Synthesis of (−)-Peyssonnoside A

Xu, B.; Liu, C.; Dai M. J. Am. Chem. Soc. 2022, 144, 19700−19703.

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2024-01-31
Step count:
22
Difficulty:
3
Streamlined Total Synthesis of Uncialamycin and Its Application to the Synthesis of Designed Analogues for Biological Investigations

Nicolaou, K. C.; Wang, Y.; Lu, M.; Mandal, D.; Pattanayak, M. R.; Yu, R.; Shah, A. A.; Chen, J. S.; Zhang, H.; Crawford, J. J.; Pasunoori, L.; Poudel, Y. B.; Chowdari, N. S.; Pan, C.; Nazeer, A.; Gangwar, S.; Vite, G.; Pitsinos, E. N. J. Am. Chem. Soc. 2016, 138, 8235–8246.

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2024-01-24
Step count:
10
Difficulty:
3
Total Synthesis of Strychnine

Lee, G. S.; Namkoong, G.; Park, J.; Chen. D. Y.-K. Chem. Eur. J. 2017, 23, 16189–16193.

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2024-01-17
Step count:
19
Difficulty:
3
Total Syntheses of Scabrolide A and Yonarolide

Serrano, R.; Boyko, Y. D.; Hernandez, L. W.; Lotuzas, A.; Sarlah, D. J. Am. Chem. Soc. 2023, 145, 8805–8809.

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2024-01-10
Step count:
17
Difficulty:
2
Enantioselective Total Synthesis of (+)-Dihydro-β-erythroidine

Clementson S.; Jessing M.; Pedersen H.; Vital P.; Kristensen J. P. J. Am. Chem. Soc. 2019, 141, 8783-8786

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2023-12-20
Step count:
27
Difficulty:
2
Bent π-Conjugation within a Macrocycle: Asymmetric Total Syntheses of Spirohexenolides A and B

Guo, L.-D.; Wu, Y.; Xu, X.; Lin, Z.; Tong, R. Angew. Chem. Int. Ed. 2023, e202316259

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2023-12-13
Step count:
13
Difficulty:
3
Site-Specific Photochemical Desaturation Enables Divergent Syntheses of Illicium Sesquiterpenes

Shen, Y.; Li, L.; Xiao, X.; Yang, S.; Hua, Y.; Wang, Y.; Zhang, Y.-W.; Zhang, Y. J. Am. Chem. Soc. 2021, 143, 3256–3263.

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2023-12-06
Step count:
16
Difficulty:
3
Total Synthesis of (+)-Fendleridine (Aspidoalbidine) and (+)-1-Acetylaspidoalbidine

Campbell, E.L.; Zuhl, M.; Liu, C.M.; Boger, D. J. Am. Chem. Soc. 2010, 132, 3009-3012.

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2023-11-29
Step count:
19
Difficulty:
2
Enatioselective Total Synthesis of the Cephalotaxus Alkaloids (-)-Fourtuneicyclidine A and B and (-)-Cephalotine B

Sheng, P-Z.; Ni, Z-B.; Li, L-L.; Wei, K.; Zhang, H.; Yang, Y-R. Org. Lett. 2023, 25, 7464-7469.

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2023-11-15
Step count:
20
Difficulty:
3
Asymmetric Synthesis of Cyclopamine, a Hedgehog (Hh) Signaling Pathway Inhibitor

Shao, A.; Liu, W.; Liu, M.; He, H.; Zhou, Q.-L.; Zhu, S.-F.; Gao, S. J. Am. Chem. Soc. 2023, 145, 25086-25092.

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2023-11-09
Step count:
22
Difficulty:
2
Enantioselective Total Synthesis of (-)-Maoecrystal V

Zheng, C.; Dubovyk, I.; Lazarski, K. E.; Thomson, R. E., J. Am. Chem. Soc. 2014, 136, 17750-17756

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2023-11-08
Step count:
16
Difficulty:
1
Total synthesis of (-)-Nummularine F

Heffner, R. J.; Jiang, J.; Joullie, M. M. J. Am. Chem. Soc. 1992, 26, 10181–10189.

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2023-11-01
Step count:
20
Difficulty:
2
Total Synthesis of dl-Coriolin

Danishefsky, S.; Zamboni, R.; Kahn, M.; Etheredge S. J. J. Am. Chem. Soc. 1980, 102, 6, 2097–2098.

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2023-10-25
Step count:
20
Difficulty:
1
Total Synthesis of (+)-Gracilamine Based on an Oxidative Phenolic Coupling Reaction and Determination of its Absolute Configuration

Odagi, M.; Yamamoto, Y.; Nagasawa, K. Angew. Chem. Int. Ed. 2018, 57, 2229-2232

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2023-10-18
Step count:
13
Difficulty:
2
Total Synthesis of (+)-Aberrarone

Wang, Y.;  Su, Y; Jia, Y. J. Am. Chem. Soc. 2023, 145, 9459–9463.

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2023-10-11
Step count:
23
Difficulty:
3
Synthesis of a limonoid, azadiradione

Corey, E. J.; Hahl, R. W. Tetrahedron Lett. 1989, 30, 3023–3026.

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2023-10-04
Step count:
8
Difficulty:
1
Total Synthesis of (±)-Trigonoliimine C via Oxidative Rearrangement of an Unsymmetrical Bis-Tryptamine

Qi, X.; Bao, H.; Tambar, U. K. J. Am. Chem. Soc. 2011, 133, 10050–10053.

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2023-09-27
Step count:
12
Difficulty:
2
Enantioselective Total Synthesis of (−)-Pavidolide B

Zhang, P.; Yan, Z.; Li, Y.; Gong, J.; Yang, Z. J. Am. Chem. Soc. 2017, 139, 13989−13992.

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2023-09-20
Step count:
12
Difficulty:
2
Synthesis of ent-Ketorfanol via a C-H Alkenylation/Torquoselective 6𝝿 Electrocyclization Cascade

Phillips, E. M.; Mesganaw, T.; Patel, A.; Duttwyler, S.; Mercado, B. Q.; Houk, K. N.; Ellman, J. A. Angew. Chem. Int. Ed. 2015, 54, 12044-12048.

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2023-09-13
Step count:
22
Difficulty:
2
Total Synthesis of the Isodon Diterpene Sculponeatin D

Moritz, B. J.; Mack, D. J.; Tong, L.; Thomson, R. J. Angew. Chem. Int. Ed. 2014, 53, 2988–2991.

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2023-09-06
Step count:
30
Difficulty:
3
Total Synthesis of Rubriflordilactone B

Yang, P.; Yao, M.; Li, J.; Li. Y; Li. A. Angew. Chem. Int. Ed. 2016, 55, 6964–6968.

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2023-08-30
Step count:
23
Difficulty:
2
Total Synthesis of Isorosthin L and Isoadenolin I

Ao, J.; Sun, C.; Chen, B.; Yu, N.; Liang, G. Angew. Chem. Int. Ed. 2022, 61, e202114489.

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2023-08-23
Step count:
25
Difficulty:
3
Scalable Total Synthesis of Portimine A and B Reveals the Basis of Their Potent and Selective Anti-cancer Acitvity

Tang, J.; Li, W.; Chiu, T.-Y.; Lou, Z.; Chong, C. T.; Wei, Q.; Martinez-Peňa, Gazaniga, N.; See, Y. Y.; Lairson, L. L.; Parker, C. G.; Baran, P. S. Chemrxiv, 2023

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2023-08-16
Step count:
30
Difficulty:
2
Total Synthesis of Lyconesidine B, a Lycopodium Alkaloid with an Oxygenated, Amine-Type Fawcettimine Core

Kurose, T.; Tsukano, C.; Nanjo, T.; Takemoto, Y. Org. Lett. 2021, 23, 676–681.

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2023-08-09
Step count:
12
Difficulty:
3
Concise asymmetric synthesis of (−)-bilobalide

Baker, M. A.; Demoret, R. M.; Ohtawa, M.; Shenvi, R. A. Nature 2019, 575, 643–646.

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2023-08-02
Step count:
22
Difficulty:
2
Enantioselective Total Synthesis of (+)-Stephadiamine

Yang, B.; Li, G.; Wang, Q.; Zhu, J. J. Am. Chem. Soc. 2023, 145, 5001–5006

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2023-07-26
Step count:
28
Difficulty:
3
Asymmetric Total Synthesis of Illisimonin A

Etling, C.; Tedesco, G.; Di Marco, A.; Kalesse, M. J. Am. Chem. Soc. 2023, 145, 7021-7029.

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2023-07-19
Step count:
16
Difficulty:
2
Total Synthesis of (+)-Fawcettidine

Kozak, J. A.; Dake, G. R. Angew. Chem. Int. Ed. 2008, 47, 4221–4223.

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2023-07-12
Step count:
12
Difficulty:
2
Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin

Hung, K.; Condakes, M.; Morikawa, T.; Maimone, T. J. J. Am. Chem. Soc. 2016, 138, 16616–16619

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2023-07-05
Step count:
20
Difficulty:
3
Total Synthesis of (-)-Sinularadiolide. A Transannular Approach

Meng, Z.; Fürstner, A. J. Am. Chem. Soc. 2019, 141, 805-819.

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2023-06-28
Step count:
11
Difficulty:
2
Assembly of the Limonoid Architecture by a Divergent Approach: Total Synthesis of (±)-Andirolide N via (±)-8α-Hydroxycarapin

Schuppe, A. W.; Newhouse, T. R. J. Am. Chem. Soc. 2017, 139, 631–634.

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2023-06-21
Step count:
19
Difficulty:
1
Enantioselective Total Synthesis of (−)-Limaspermidine and (−)-Kopsinine by a Nitroaryl Transfer Cascade Strategy

Horst, B.; Verdoorn, D. S.; Hennig, S.; van der Heijden, G.; Ruijter, E. Angew. Chem. Int. Ed. 2022, 61, e202210592.

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2023-06-14
Step count:
21
Difficulty:
2
Total Synthesis of (±)-Waihoensene

Lee, H.; Kang. T.; Lee H.-Y. Angew. Chem. Int. Ed. 2017, 56, 8254-8257.

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2023-06-07
Step count:
19
Difficulty:
2
Total Synthesis of (–)-Gardmultimine A

Che, P.; Yang, H.; Zhang, H.; Chen, W.; Zhang, Z.; Zhang, J.; Li, H.; Wang, X.; Xie, X.; She, X. Org. Lett. 2020, 22, 2022–2025

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2023-05-31
Step count:
17
Difficulty:
1
Asymmetric Total Synthesis of (+)-6-epi-Castanospermine by the Stereoselective Formation of a syn,anti Acetylenic 2-Amino-1,3-diol Stereotriad

Louvel, J.; Botuha, C.; Chemla, F.; Demont, E.; Ferreira, Fr.; Pérez-Luna, A.  Eur. J. Org. Chem. 2010, 2921–2926.

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2023-05-24
Step count:
13
Difficulty:
3
A Concise Synthesis of Pleurotin Enabled by a Nontraditional C-H Epimerization

Hoskin, J. F.; Sorensen, E. J. J. Am. Chem. Soc. 2022, 144, 14042-14046

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2023-05-17
Step count:
18
Difficulty:
1
Total Synthesis of the Tetracyclic Pyridinium Alkaloid epi-Tetradehydrohalicyclamine B

Dalling, A. G.; Späth, G.; Fürstner, A. Angew. Chem. Int. Ed. 2022, 61, e202209651.

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2023-05-10
Step count:
15
Difficulty:
2
Combined C−H Activation/Cope Rearrangement as a Strategic Reaction in Organic Synthesis:  Total Synthesis of (−)-Colombiasin A and (−)-Elisapterosin B

Davies, H. M. L.; Dai, X.; Long, M. S. J. Am. Chem. Soc. 2006, 128, 2485–2490.

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2023-05-03
Step count:
18
Difficulty:
2
Total Synthesis of the Akuammiline Alkaloid Picrinine

Smith, J. M.; Moreno, J.; Boal, B. W.; Garg, N. K. J. Am. Chem. Soc. 2014, 136, 4504–4507.

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2023-04-26
Step count:
14
Difficulty:
1
10-Step Asymmetric Total Synthesis and Stereochemical Elucidation of (+)-Dragmacidin D

Jackson, J. J.; Kobayashi, H.; Steffens, S. D.; Zakarian, A. Angew. Chem. Int. Ed. 2015, 54, 9971−9975.

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2023-04-19
Step count:
15
Difficulty:
2
Total Synthesis of Bipolamine I

Qiu, X.; Pierce, J. G. J. Am. Chem. Soc. 2022, 144, 12638–12641.

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2023-04-12
Step count:
11
Difficulty:
1
The Total Synthesis of (+)-Shearilicine

Kim, D.; Zhy, Y.; Harada, S.; Aguilar, I.; Cuomo, A.; Wang, M.; Newhouse, T. R. J. Am. Chem. Soc. 2023, 145, 4394−4399.

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2023-04-05
Step count:
18
Difficulty:
1
Total Synthesis of Abyssomicin C and atrop-Abyssomicin C

Nicolaou, K. C.; Harrison, S. T. Angew. Chem. Int. Ed. 2006, 45, 3256–3260.

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2023-03-29
Step count:
20
Difficulty:
3
Total Synthesis of Dapholdhamine B and Dapholdamine B Lactone

Guo, L.-D.; Hou, J.; Tu, W.; Zhang, Y.; Zhang, Y.; Chen, L.; Xu, J. J. Am. Chem. Soc. 2019, 141, 11613–11720.

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2023-03-22
Step count:
28
Difficulty:
2
Enantioselective Synthesis of (−)-Maoecrystal V by Enantiodetermining C–H Functionalization

Lu, P.; Mailyan, A.; Gu, Z.; Guptill, D. M.; Wang, H.; Davies, H. M. L.; Zakarian, A. J. Am. Chem. Soc. 2014, 136, 17738–17749.

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2023-03-15
Step count:
28
Difficulty:
2
Total Synthesis of Vilmoraconitine

Ji, J.; Chen, J.; Qin, S.; Li, W.; Zhao, J.; Li, G.; Song, H.; Liu, X.; Qin, Y. J. Am. Chem. Soc. 2023, 145, 3903-3908.

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2023-03-08
Step count:
28
Difficulty:
3
Total Synthesis of Ginkgolide C and Formal Syntheses of Ginkgolides A and B

Hébert, M.; Bellavance, G.; Barriault, L. J. Am. Chem. Soc. 2022, 144, 17792-17796.

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2023-03-01
Step count:
23
Difficulty:
2
Total Synthesis of Hirsutellone B

Nicolaou, K. C.; Sarlah, D.; Wu, T. R.; Zhan, W. Angew. Chem. Int. Ed. 2009, 48, 6870–6874.

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2023-02-22
Step count:
17
Difficulty:
2
Total Synthesis of (-)-Daphenylline

Xu, B.; Wang, B.; Xun, W.; Qiu, F. G. Angew. Chem. Int. Ed. 2019, 58, 5754–5757.

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2023-02-15
Step count:
31
Difficulty:
3
Total Synthesis of Yuzurine-type Alkaloid Daphgraciline

Li, L.-X.; Min, L.; Yao, T.-B.; Ji, S.-X.; Qiao, C.; Tian, P.-L.; Sun, J.; Li, C.-C. J. Am. Chem. Soc. 2022, 144, 18823–18828.

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2023-02-09
Step count:
32
Difficulty:
3
Total Synthesis of Puberuline C

Shimakawa, T.; Nakamura, S.; Asai, H.; Hagiwara, K.; Inoue, M. J. Am. Chem. Soc. 2023, 145, 600–609.

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2023-02-01
Step count:
18
Difficulty:
2
Enantioselective Total Synthesis of (+)-Aberrarone

Amberg, W. M.; Carreira, E. M. J. Am. Chem. Soc. 2022, 144, 15475–15479.

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2023-01-26
Step count:
11
Difficulty:
2
Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G

Hu, L.; Rawal, V. H. J. Am. Chem. Soc. 2021, 143, 10872–10875.

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2023-01-15
Step count:
21
Difficulty:
2
Total Synthesis of Farnesin through an Excited-State Nazarov Reaction

Que, H. Y.; Shao, H.;  He, H.; Gao, S. Angew. Chem. Int. Ed. 2020, 59, 7444–7449.

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2022-12-08
Step count:
21
Difficulty:
1
Enantioselective Total Synthesis of (+)-Tricycloclavulone

Ito,H.;* Hasegawa, M.; Takenaka, Y.; Kobayashi, T.; Iguchi, K.* J. Am. Chem. Soc. 2004, 126, 4520–4521.

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2022-12-01
Step count:
11
Difficulty:
2
An eight-step gram-scale synthesis of (−)-jiadifenolide

Lu, H.; Martinez, M.; Shenvi, R. Nat. Chem. 2015, 7, 604–607.

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2022-11-22
Step count:
16
Difficulty:
1
Asymmetric Total Syntheses of Hypoestin A, Albolic Acid, and Ceroplastol II

Wang, Y.; Xu, K.; Min, L.; Li, C. J. Am. Chem. Soc. 2022, 144, 10162–10167.

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2022-11-10
Step count:
14
Difficulty:
1
Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship

Miloserdov, F. M.; Kirillova, M. S.; Muratore, M. E.; Echavarren, A. M. J. Am. Chem. Soc. 2018, 140, 5393–5400.

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[Key CDX]
2022-11-03
Step count:
20
Difficulty:
2
Tandem Decarboxylative Cyclization/Alkenylation Strategy for Total Syntheses of (+)-Longirabdiol, (–)-Longirabdolactone, and (–)-Effusin

Zhang, J.;Li, Z.; Zhuo, J.; Cui, Y.; Han, T.; Li, C. J. Am. Chem. Soc. 2019, 141, 8372–8380.

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[Problem CDX]
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[Key CDX]
2022-10-27
Step count:
14
Difficulty:
1
14-Step Synthesis of (+)-Ingenol from (+)-3-Carene

Jørgensen, L.; McKerrall, S. J.; Kuttruff, C. A.; Ungeheuer, F.; Felding, J.; Baran, P. S. Science, 2013, 341, 878–882

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-10-20
Step count:
29
Difficulty:
3
Asymmetric Total Synthesis of Hispidanin A

Deng, H.; Cao, W.; Liu, R.; Zhang, Y.; Liu, B. Angew. Chem. Int. Ed. 2017, 56, 5849–5852.

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[Problem CDX]
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[Key CDX]
2022-10-13
Step count:
23
Difficulty:
2
Total Synthesis of Rameswaralide Utilizing a Pharmacophore-Directed Retrosynthetic Strategy

Truax, N. J.;  Ayinde, S.; Liu, J. O.; Romo, D. J. Am. Chem. Soc. 2022, 144, 18575-18585

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-09-22
Step count:
28
Difficulty:
3
Enantioselective Total Synthesis of Cotylenin A

Uwamori, M.; Osada, R.; Sugiyama, R.; Nagatani, K.; Nakada, M. J. Am. Chem. Soc. 2020, 142, 5556–5561.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-09-08
Step count:
25
Difficulty:
2
Synthesis of (+)-CP-263,114

Chen, C.; Layton, M. E.; Sheehan, S. M.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 7424-7425.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-09-01
Step count:
22
Difficulty:
2
Enantioselective Total Synthesis of (+)-Euphorikanin A

Classen, M. J.; Böcker, M. N. A.; Roth, R.; Amberg, W. M.; Carreira, E. M. J. Am. Chem. Soc. 2021, 143, 8261–8265.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-08-25
Step count:
24
Difficulty:
3
Total Syntheses of (–)-Acutumine and (–)-Dechloroacutumine

King, S. M.; Calandra, N. A.; Herzon, S. B. Angew. Chem. Int. Ed. 2013, 52, 3642–3645.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-08-18
Step count:
13
Difficulty:
3
Total Synthesis of (+)-6-epi-Ophiobolin A

Thach, D. Q.; Brill, Z. G.; Grover, H. K.; Esguerra, K. V.; Thompson, J. K.; Maimone, T. J. Angew. Chem. Int. Ed. 2020, 59, 1532–1536.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-08-11
Step count:
17
Difficulty:
3
Asymmetric Total Syntheses of (+)-Davisinol and (+)-18-Benzoyldavisinol: A HAT-Initiated Transannular Redox Radical Approach

Yu, K.; Yao, F.; Zeng, Q.; Xie, H.; Ding, H. J. Am. Chem. Soc. 2010, 132, 8506–8512

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-07-25
Step count:
16
Difficulty:
1
Transition-Metal-Mediated Chemo- and Stereoselective Total Synthesis of (−)-Galanthamine

Miller, I. R.; McLean, N. J.; Moustafa, G. A. I.; Ajavakom, V.; Kemp, S. C.; Bellingham, R. K.; Camp, N. P.; Brown, R. C. D. J. Org. Chem. 2022, 87, 1325-1334

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-07-18
Step count:
14
Difficulty:
1
Total Synthesis of (+)-Cochlearol B by an Approach Based on a Catellani Reaction and Visible-Light-Enabled [2+2] Cycloaddition

Richardson, A. D.; Trenton, R. V; Traficante, E. F.; Glover, K. J.; Schindler, C. S. Angew. Chem. Int. Ed. 2022, e202201213.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-07-11
Step count:
13
Difficulty:
2
Total Syntheses of (+)-Aquatolide and Related Humulanolides

Takao, K.-I.; Kai, H.; Yamada, A.; Fukushima, Y.; Komatsu, D.; Ogura, A.; Yoshida, K. Angew. Chem. Int. Ed. 2019, 58, 9851–9855.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-06-27
Step count:
19
Difficulty:
2
Total Synthesis of Daphenylline, Daphnipaxianine A, and Himalenine D

Chen, Y.; Zhang, W.; Ren, L.; Li, J.; Li, A. Angew. Chem. Int. 2018, 130, 964–968.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-06-13
Step count:
16
Difficulty:
1
A Chlorine-Atom-Controlled Terminal-Epoxide-Initiated Bicyclization Cascade Enables a Synthesis of the Potent Cytotoxins Haterumaimides J and K

Michalak, S. E.; Nam, S.; Kown, D. M.; Horne, D. A.; Vanderwal, C. D, J. Am. Chem. Soc. 2019, 141, 9202–9206

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-06-06
Step count:
18
Difficulty:
1
Asymmetric Total Synthesis of (+)-Mannolide C

Ao, Q.; Zhang, H-J.; Zheng, J.; Chen, X.; Zhai, H. Angew. Chem. Int. Ed. 2021, 60, 21267-21271

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-05-30
Step count:
16
Difficulty:
1
Total Synthesis of (±)-Isophellibiline

Funk, R. L.; Belmar, J. Tetrahedron Lett. 2012, 53, 176–178.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-05-16
Step count:
17
Difficulty:
2
Asymmetric Total Synthesis of (2R)‑Hydroxynorneomajucin, a Norsesquiterpene from Illicium jiadifengpi

Dooley, C.; Rychnovsky, S. Org. Lett. 2022, 24, 3411–3415.

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[Problem CDX]
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[Key CDX]
2022-05-09
Step count:
14
Difficulty:
1
Deconstructive Asymmetric Total Synthesis of Morphine-Family Alkaloid (-)-Thebainone A

Hou, S.-H.; Prichina, A. Y.; Dong, G. Angew. Chem. Int. Ed. 2021, 60, 13057–13064.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-05-02
Step count:
14
Difficulty:
1
Asymmetric Total Synthesis of Laurallene

Yoshimura, F.; Okada, T.; Tanino, K. Org. Lett. 2019, 21, 559-562

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-04-25
Step count:
12
Difficulty:
1
β-Ketoesters as Mono- or Bisnucleophiles: A concise Enantioselective Total synthesis of (-)-Englerin A and B

Guo, L.; Plietker, B. Angew. Chem. Int. Ed. 2019, 58, 8346-8350.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-04-18
Step count:
17
Difficulty:
2
Total Synthesis of (±)-Perophoramide

Fuchs, J. R.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 5068-5069.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-04-11
Step count:
20
Difficulty:
2
The Total Synthesis of (±)-11-O-Debenzoyltashironin

Cook, S. P.; Polara, A.; Danishefsky, S. J. J. Am. Chem. Soc. 2006, 128, 16440–16441.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-04-04
Step count:
25
Difficulty:
2
Total Synthesis of Vinigrol

T. J. Maimone, J. Shi, S. Ashida, P. S. Baran, J. Am. Chem. Soc. 2009, 131, 17066-17067.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-03-28
Step count:
31
Difficulty:
3
Total Synthesis of Gukulenin B via Sequential Tropolone Functionalizations

Nicolaou, K. C.; Yu, R.; Lu, Z.; Alvarez, F. G. J. Am. Chem. Soc. 2022, 144, 5190–5196

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[Problem CDX]
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[Key CDX]
2022-03-21
Step count:
21
Difficulty:
2
Synthesis of Swinhoeisterol A, Dankasterone A and B, and Periconiastone A by Radical Framework Reconstruction

Duecker, F. L.; Heinze, R. C.; Heretsch, H. J. Am. Chem. Soc. 2020, 142, 104-108.

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[Problem CDX]
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[Key CDX]
2022-03-14
Step count:
34
Difficulty:
3
Asymmetric Total Synthesis of Norzoanthamine

Xin, Z.; Wang, H.; He, H.; Zhao, X.; Gao, S. Angew. Chem. Int. Ed. 2021, 60, 12807-12812.

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[Problem CDX]
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[Key CDX]
2022-03-07
Step count:
29
Difficulty:
3
Bidirectional Total Synthesis of Phainanoid A via Strategic Use of Ketones

Xie, J.; Liu, X.; Zhang, N.; Choi S.; Dong, G. J. Am. Chem. Soc. 2021, 143, 19311–19316.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-02-28
Step count:
28
Difficulty:
2
Asymmetric Total Synthesis of Indole Diterpenes Paspalicine, Paspalinine, and Paspalinine-13-ene

Guo, L.-D.; Xu, Z.; Tong, R. Angew. Chem. Int. Ed. 2022, 61, e202115384.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-02-21
Step count:
24
Difficulty:
3
Total Synthesis of (−)-Rhodomollanol A

Gao, J.; Rao, P.; Xu, K.; Wang, S.; Wu, Y.; He, C.; Ding, H. J. Am. Chem. Soc. 2020, 142, 4592-4597.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-02-14
Step count:
23
Difficulty:
1
Total Synthesis of (±)-Leonuketal

Grant, P. S.; Furkert, D. P.; Brimble, M. A. Org. Lett. 2020, 22, 8735-8740.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-02-07
Step count:
18
Difficulty:
3
Asymmetric Total Synthesis of Shizukaol J, Trichloranoid C and Trishizukaol A

Wang, X.; Wang, Z.; Ma, X.; Huang, Z.; Sun, K.; Gao, X.; Fu, S.; Liu, B. Angew. Chem. Int. Ed. 2022, ASAP.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-01-31
Step count:
14
Difficulty:
2
Total Synthesis of (of (−)-Daphnezomines A and B

Xu, G.; Wu, J.; Li, L.; Lu, Y.; Li, C. J. Am. Chem. Soc. 2020, 142, 15240-15245.

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[Problem CDX]
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[Key CDX]
2022-01-24
Step count:
15
Difficulty:
2
A Short Synthesis of Delavatine A Unveils New Insights into Site-Selective Cross-Coupling of 3,5-Dibromo-2-pyrone

Palani, V.; Hugelshofer, C. L.; Kevlishvili, L.; Liu, P.; Sarpong, R. J. Am. Chem. Soc. 2019, 141, 2652−2660.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-01-17
Step count:
15
Difficulty:
1
A biomimetic total synthesis of (+)-intricarene

Tang, B.; Bray, C. D.; Pattenden G. Tetrahedron Lett. 2006, 47, 6401–6404.

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2022-01-10
Step count:
15
Difficulty:
1
Enantioselective Total Synthesis of (+)-Hinckdentine A via a Catalytic Dearomatization Approach

Douki, K.; Ono, H.; Taniguchi, T.; Shimokawa, J.; Kitamura, M.; Fukuyama, T. J. Am. Chem. Soc. 2016, 138, 14578−14581

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[Key PDF]
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[Problem CDX]
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[Key CDX]
2021-12-20
Step count:
13
Difficulty:
2
Ir-Catalyzed Asymmetric Total Syntheses of Bisdehydrotuberostemonine D, Putative Bisdehydrotuberostemonine E and Structural Revision of the Latter

Deng, Y.; Liang, X.; Wei, K.; Yang, Y. R. J. Am. Chem. Soc. 2021, 143, 20622–20627

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[Problem CDX]
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[Key CDX]