Synthesis Club Roadmap Problems
April 23rd, 2024 – Enantioselective Synthesis of Pactamycin, a Complex Antitumor Antibiotic
![](/en/drugs/download/Synthesis Quizzes/2024_02_20_Tetrodotoxin/Pactamycin.jpg)
Justin T. Malinowki, Robert J. Sharpe, Jeffrey S. Johnson
Science, 2013, 340, 180–182.
April 9th, 2024 – Concise Total Synthesis of Complanadine A
![](/en/drugs/download/Synthesis Quizzes/2024_02_20_Tetrodotoxin/structure-Complanadine-A.jpg)
D. Ma, B. S. Martin, K. S. Gallagher, T. Saito, and M. Dai
Synthesis 2024; 56(01): 107-117; J. Am. Chem. Soc. 2021, 143, 40, 16383–16387.
February 20th, 2024 – A concise synthesis of tetrodotoxin
![](/en/drugs/download/Synthesis Quizzes/2024_02_20_Tetrodotoxin/Tetrodotoxin_0.jpg)
Konrad, D.B., Rühmann, K., Ando, H., Hetzler, B.E., Strassner, N., Houk, K.N., Matsuura, B.S., Trauner, D. Science, 2022, 377, 411–415
January 24th, 2024 – Navigating Excess Complexity: Total Synthesis of Daphenylline
![](/en/drugs/download/Synthesis Quizzes/2024_01_24_Daphenylline/daphenylline_0.jpg)
Wright, BB. A., Regni, A., Chaisan, N., Sarpong, R. J. Am. Chem. Soc. 2024, doi: 10.1021/jacs.3c12953
November 21st, 2023 – Total Synthesis of Aleutianamine
![](/en/drugs/download/Synthesis Quizzes/2023_11_21_Aleutianamine/Aleutianamine-Image.jpg)
Hao Yu, Zachary P. Sercel, Samir P. Rezgui, Jonathan Farhi, Scott C. Virgil, Brian M. Stoltz
J. Am. Chem. Soc. 2023 DOI: 10.1021/jacs.3c10212
October 24th, 2023 – Total Synthesis of Metaphanine
![](/en/drugs/download/Synthesis Quizzes/2023_10_24_Metaphanine/Metaphanine.jpg)
Ya-Kui Sun, Jin-Bao Qiao, Yu-Meng Xin, Qin Zhou, Zhi-Hua Ma, Hui Shao, Yu-Ming Zhao
Angew. Chem. Int. Ed. 2023, 62, e202310917.
October 10th, 2023 – Asymmetric Total Synthesis of Illisimonin A
![](/en/drugs/download/Synthesis Quizzes/2023_09_26_Ineleganolide/Illisimonin-A.jpg)
Etling, C., Tedesco, G., Di Marco, A., Kalesse, M. J. Am. Chem. Soc., 2023, 145, 7021–7029
September 26th, 2023 – A Convergent Total Synthesis of (+)-Ineleganolide
![](/en/drugs/download/Synthesis Quizzes/2023_09_26_Ineleganolide/+-ineleganolide.jpg)
Gross, Benjamin M.; Han, Seo-Jung; Virgil, Scott C.;Stoltz, Brian M. J. Am. Chem. Soc. 2023, 7763 – 7767
September 11th, 2023 – Enantioselective Total Synthesis of Sacrolide A
![](/en/drugs/download/Synthesis Quizzes/2023_08_08_Stempeliopidine/Sacrolide-A.jpg)
Tomoyo Mohri, Yusuke Ogura, Ryo Towada, Shigefumi Kuwahara, Tetrahedron Letters, 2017, 58, 4011-4013
August 8th, 2023 – Total Synthesis of Stempeliopidine and Non-Natural Stereoisomers through a Convergent Petasis Borono–Mannich Reaction
![](/en/drugs/download/Synthesis Quizzes/2023_08_08_Stempeliopidine/strempeliopidine.jpg)
Rand, A.W.; Gonzalez, K.J.; Reimann, C.E.; Virgil, S.C; Stoltz, B.M. J. Am. Chem. Soc. 2023, 145, 7278–7287.
July 18th, 2023 – Enantioselective Total Synthesis of (−)-Caulamidine A
![](/en/drugs/download/Synthesis Quizzes/2023_07_18_Caulamidine/--caulamidine-A.jpg)
Zhouyang Zhu and Thomas J. Maimone J. Am. Chem. Soc. 2023, 145, 14215–14220.
June 20th, 2023 – Total Synthesis of (+)-Waixenicin A
![](/__we_thumbs__/89496_1_+-Waixenicin-A.jpg)
Steinborn, C., Huber, T., Lichtenegger, J., Plangger, I., Wurst, K., & Magauer, T. J. Am. Chem. Soc. 2023, 145, 21, 11811–11817.
May 5th, 2023 – Synthesis of Eupalinilide E, a Promoter of Human Hematopoietic Stem and Progenitor Cell Expansion
![](/en/drugs/download/Synthesis Quizzes/2023_05_23_Eupalinilide/eupalinilide-E.jpg)
Johnson, T.C., Chin, M.R., Han, T., Shen, J.P., Rana, T., Siegel, D. J. Am. Chem. Soc. 2016, 138, 18, 6068–6073
April 11th, 2023 – Enantioselective Total Synthesis of Lycopodine
![](/en/drugs/download/Synthesis Quizzes/2023_04_11_Lycopodine/lycopodine_0.jpg)
Hua Yang, Rich G. Carter* and Lev N. Zakharov J. Am. Chem. Soc. 2008, 130, 29, 9238–9239
March 2023 – Total Synthesis and Structure Assignment of (+)-Hexacyclinol
![](/en/drugs/download/Synthesis Quizzes/2023_03_Hexacyclinol/Structure.jpg)
Porco, J.A., Jr.; Su, S.; Lei, X.; Bardhan, S.; Rychnovsky, S.D. Angew. Chem. Int. Ed. 2006, 35, 5790 – 5792
February 28th, 2023 – Total Synthesis of Vilmoraconitine
![](/en/drugs/download/Synthesis Quizzes/2023_02_28_Vilmoraconitine/Structure.jpg)
Ji, J; Chen, J; Qin, S; Li, W; Zhao, J; Li, G; Song, H; Liu, X-Y; Qin, Y J. Am. Chem. Soc. 2023, 3903–3908
December 20th, 2022 – Total Synthesis of Yuzurine-type Alkaloid Daphgraciline
![](/en/drugs/download/Synthesis Quizzes/2022_12_20_Daphgraciline/daphgraciline.jpg)
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.
December 6th, 2022 – The First Asymmetric Synthesis of a Lycorine Alkaloid. Total Synthesis of (+)-1-Deoxylycorine
![](/en/drugs/download/Synthesis Quizzes/2022_12_06_Deoxylycorine/deoxylycorine.jpg)
A. G. Schultz, M. A. Holoboski, M. S. Smyth J. Am. Chem. Soc, 1993, 115, 7904–7905.
December 10th, 2019 – Scalable Total Synthesis of (–)-Vinigrol
![](/en/drugs/download/Synthesis Quizzes/2019_12_10_Vinigrol/Vinigrol.jpg)
X. Yu, L. Xiao, Z. Wang, T. Luo J. Am. Chem. Soc. 2019, 141, 3440–13443.
November 26th, 2019 – Total Synthesis of (–)-Crinipellin A
![](/en/drugs/download/Synthesis Quizzes/2019_11_26_Crinipellin A/CrinipellinA_new.jpg)
T. T. Kang, S.B. Song, W.-Y. Kim, B. G. Kim, H.-Y. Lee J. Am. Chem. Soc. 2014, 136, 10274–10276
November 12th, 2019 – Highly Efficient Total Synthesis of the Marine Natural Products (+)-Avarone, (+)-Avarol, (-)-Neoavarone, (-)-Neoavarol and (+)-Aureol
![](/en/drugs/download/Synthesis Quizzes/2019_11_12_Aureol/+-aureol.jpg)
J. Sakurai, T. Oguchi, K. Watanabe, H. Abe, S. Kanno, M. Ishikawa, and T. Katoh Chem. Eur. J. 2008, 14, 829 – 837.
October 15th – A 16-step Synthesis of the Isoryanodane Diterpene (+)-Perseanol
![](/__we_thumbs__/72325_1_perseanol.jpg)
A. Han, Y. Tao, S. E. Reisman Nature, 2019, 573, 563–568.
October 1st – The Furan Shuffling Hypothesis: A Biogenetic Proposal for Eremophilane Sesquiterpenoids
![](/en/drugs/download/Synthesis Quizzes/2019_10_01_Furan Shuffling/products.jpg)
N. Lardon, R. Liffer, A. Linder, K. Gademann Angew. Chem. Int. Ed. 2019, 58, 7004–7007.
September 17th, 2019 – Second-generation Synthesis of Salvinorin A
![](/en/drugs/download/Synthesis Quizzes/2019_09_17_Salvinorin A/Salvinorin-Picture.png)
H. Hagiwara, Y. Suka, T. Nojima, T. Hoshi, T. Suzuki Tetrahedron, 2009, 65, 4820–4825.
May 16th, 2019 – Biomimetic Total Synthesis of (±)-Basiliolide B
![](/en/drugs/download/Synthesis Quizzes/2019_05_17_Basiliolide B/bailiolide-B.jpg)
X. Liang, L. Zhou, L. Min, W. Ye, W. Bao, W. Ma, Q. Yang, F. Qiao, X. Zhang, C. -S. Lee Angew. Chem. Int. Ed. 2014, 53, 11294–11297.
April 25, 2019 – Total Synthesis and Determination of the Absolute Configuration of Frondosin B
![](/en/drugs/download/Synthesis Quizzes/2019_04_25_Frondosin B/Frondosin.jpg)
M. Inoue, M.W. Carson, A.J. Frontier, S.J. Danishefsky J. Am. Chem. Soc. 2001, 123, 1878–1889.
April 18th, 2019 – Total Synthesis of (±)-Acremoxanthone A
![](/en/drugs/download/Synthesis Quizzes/2019_04_18_Acremonxanthone A/Acremoxanthone-A.jpg)
S.D. Hombo, S.V. Pronin, J. Am. Chem. Soc. 2018, 140, 5065–5068.
April 2nd, 2019 – Asymmetric Total Synthesis of (20S)-Camptothecin using a Chiral Auxiliary Strategy
![](/en/drugs/download/Synthesis Quizzes/2019_04_02_Camptothecin/camptothecin.jpg)
A. Liu, M. Liu, G. Huang, F. -e. Chen Tetrahedron, 2019, Ahead of print.
March 12th, 2019 – Synthesis of Rhazinicine by a Metal-Catalyzed C–H Bond Functionalization Strategy
![](/en/drugs/download/Synthesis Quizzes/2019_03_11_Rhazinicin/rhazinicine.jpg)
E. M. Beck, R. Hatley, M. J. Guant Angew. Chem. Int. Ed. 2008, 47, 3004–3007.
February 26th, 2019 – Total Synthesis of (+)-Dendrowardol C
![](/en/drugs/download/Synthesis Quizzes/2019_02_26_Dendrowardol C/dendrowardol_C.jpg)
H. Wolleb, E. M. Carreira Angew. Chem. Int. Ed. 2017, 56, 10890–10893.
February 5th, 2019 – The Wood, Baran, and Schindler syntheses of the Herqulines
![](/en/drugs/download/Synthesis Quizzes/2019_02_05_Herqulines B and C/Herqulines-B-and-C.jpg)
J.B. Cox, A. Kimishima, J.L.Wood J. Am. Chem. Soc. 2019, 141, 25–28.
C. He, T.P. Stratton, P.S. Baran J. Am. Chem. Soc. 2019, 141, 29–32.
X. Zhu, C.C. McAtee, C.S. Schindler ChemRxiv: doi.org/10.26434/chemrxiv.7505654.v1
January 21st, 2019 –Total synthesis of Repraesentin F and Configuration Reassignment by a Gold(I)-Catalyzed Cyclization Cascade
![](/en/drugs/download/Synthesis Quizzes/2019_01_21_Repraesentin F/repraesentinF.jpg)
Ferrer, S.; Echabarren, A. Org. Lett. 2018, 20, 5784–5788.
January 7th, 2019–An Enantioselective Total Synthesis of (+)-Duocarmycin SA
![](/en/drugs/download/Synthesis Quizzes/2019_01_07_Duocarmycin SA/duocamycin.jpg)
Schmidt, M.A.; Simmons, E.M.; Wei, C.S.; Hyunsoo Park, H.; Eastgate, M.D. J. Org. Chem. 2018, 83, 3928–3940.
December 11, 2018–A Total Synthesis of Bifidenone
![](/en/drugs/download/Synthesis Quizzes/2018_12_11_Bifidenone/bifidinone.jpg)
Huang, Z.; Williams, R.B.; O'Neil-Johnson, M.; Eldridge, G.R.; Mangette, J.E.; Starks, C.M. J. Org. Chem. 2017, 82, 4235–4241.
November 27, 2018–Enantioselective Total Syntheses of Welwitindolinone A and Fischerindoles I and G
![](/en/drugs/download/Synthesis Quizzes/2018_11_27_Welwitindolinone A/Welwitindolinone-A.jpg)
Baran, P.S.; Richter, J.M. J. Am. Chem. Soc. 2005, 127, 15394–15396.
October 30, 2018–Synthesis of Bromodomain and Extra-Terminal Domain (BET) Inhibitor GSK340
![](/en/drugs/download/Synthesis Quizzes/2018_10_30_GSK340/GSK340.jpg)
Law, R.P., Atkinson, S.J., Bamborough, P., Chung, C.-w., Demont, E.H., Gordon, L.J., Lindon, M., Prinjha, R.K., Watson, A.J.B., Hirst, D.J. J. Med. Chem. 2018, 16, 4317–4334.
October 16, 2018–Total Synthesis of the Norhasubanan Alkaloid Stephadiamine
![](/en/drugs/download/Synthesis Quizzes/2018_10_16_Stephadiamine/stephadimaine-molecule.jpg)
Hartrampf, N.; Winter, N.; Pupo, G.; Stoltz, B.M.; Trauner, D. J. Am. Chem. Soc. 2018, 140, 8675–8680.
October 2, 2018–Total Synthesis and Absolute Stereochemical Assignment of the Insecticidal Metabolites Yaequinolones J1 and J2
![](/en/drugs/download/Synthesis Quizzes/2018_10_02_Yaequinolone J1/Yaequinolone_J1.jpg)
Vece, V.; Jakkepally, S.; Hanessian, S. Org. Lett. 2018, 20, 4277–4280.
September 18, 2018--Industrial and Academic Syntheses of Oseltamivir (Tamiflu)
![](/en/drugs/download/Synthesis Quizzes/2018_09_18_Tamiflu/oseltamivir.jpg)
Rohloff, J.C. et al. J. Org. Chem. 1998, 63, 4545–4550.
Ishikawa, H., Suzuki, T., Hayashi, Y. Ang. Chem. Int. Ed. 2009, 1304–1307.
May 29, 2018–Total Syntheses of (−)-Englerins A/B, (+)-Orientalols E/F, and (−)-Oxyphyllol
![](/__we_thumbs__/68074_1_Englerin-A.jpg)
Liu, P.; Cui, Y.; Chen, K.; Zhou, X.; Pan, W.; Ren, J.; Wang, Z. Org. Lett. 2018, 20, 2517–2521.