Synthesis Club Roadmap Problems
April 23rd, 2024 – Enantioselective Synthesis of Pactamycin, a Complex Antitumor Antibiotic
Justin T. Malinowki, Robert J. Sharpe, Jeffrey S. Johnson
Science, 2013, 340, 180–182.
April 9th, 2024 – Concise Total Synthesis of Complanadine A
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
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
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
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
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
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
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
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
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
Zhouyang Zhu and Thomas J. Maimone J. Am. Chem. Soc. 2023, 145, 14215–14220.
June 20th, 2023 – Total Synthesis of (+)-Waixenicin A
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
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
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
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
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
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
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
X. Yu, L. Xiao, Z. Wang, T. Luo J. Am. Chem. Soc. 2019, 141, 3440–13443.
November 26th, 2019 – Total Synthesis of (–)-Crinipellin A
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
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
A. Han, Y. Tao, S. E. Reisman Nature, 2019, 573, 563–568.
October 1st – The Furan Shuffling Hypothesis: A Biogenetic Proposal for Eremophilane Sesquiterpenoids
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
H. Hagiwara, Y. Suka, T. Nojima, T. Hoshi, T. Suzuki Tetrahedron, 2009, 65, 4820–4825.
May 16th, 2019 – Biomimetic Total Synthesis of (±)-Basiliolide B
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
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
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
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
E. M. Beck, R. Hatley, M. J. Guant Angew. Chem. Int. Ed. 2008, 47, 3004–3007.
February 26th, 2019 – Total Synthesis of (+)-Dendrowardol C
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
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
Ferrer, S.; Echabarren, A. Org. Lett. 2018, 20, 5784–5788.
January 7th, 2019–An Enantioselective Total Synthesis of (+)-Duocarmycin SA
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
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
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
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
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
Vece, V.; Jakkepally, S.; Hanessian, S. Org. Lett. 2018, 20, 4277–4280.
September 18, 2018--Industrial and Academic Syntheses of Oseltamivir (Tamiflu)
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
Liu, P.; Cui, Y.; Chen, K.; Zhou, X.; Pan, W.; Ren, J.; Wang, Z. Org. Lett. 2018, 20, 2517–2521.