Synfacts 2020; 16(06): 0617
DOI: 10.1055/s-0040-1706993
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Total Synthesis of (+)-Waihoensene

Erick M. Carreira
Moritz J. Classen
Qu Y, Wang Z, Zhang Z, Zhang W, Huang J. * Yang Z. * Peking University Shenzen Graduate School, Peking University, Beijing, and Shenzen Bay Laboratory, P. R. of China
Asymmetric Total Synthesis of (+)-Waihoensene.

J. Am. Chem. Soc. 2020;
142: 6511-6515
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15. Mai 2020 (online)



Huang, Yang, and co-workers report the asymmetric synthesis of (+)-waihoensene in 15 steps. Waihoensene features a congested [6,5,5,5] tetracyclic core, containing four contiguous quaternary carbons and a cis-fused six-membered ring.



In five steps, enone A is transformed into G, which undergoes diastereoselective Conia-ene reaction to H. Enyne H is elaborated to J through a Pauson–Khand reaction, followed by a nickel-catalyzed 1,4-addition. Reduction of the exocyclic double bond is achieved by Fe(acac)3/PhSiH3-mediated intramolecular HAT reaction to give N. Shortly after the publication of this synthesis, Snyder and co-workers reported another synthesis of this natural product following a very similar strategy (Angew. Chem. Int. Ed. 2020, DOI: 10.1002/anie.202004177).