Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

A convergent, nine‐step (LLS), enantioselective synthesis of α‐cyclopiazonic acid and related natural products is reported. The route features a) an enantioselective aziridination of an imine with a chiral sulfur ylide; b) a bioinspired (3+2)‐cycloaddition of the aziridine onto an alkene; and c) ins...

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Detalles Bibliográficos
Autores principales: Zhurakovskyi, Oleksandr, Türkmen, Yunus E., Löffler, Lorenz E., Moorthie, Vijayalakshmi A., Chen, C. Chun, Shaw, Michael A., Crimmin, Mark R., Ferrara, Marco, Ahmad, Mushtaq, Ostovar, Mehrnoosh, Matlock, Johnathan V., Aggarwal, Varinder K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5817397/
https://www.ncbi.nlm.nih.gov/pubmed/29265694
http://dx.doi.org/10.1002/anie.201712065
Descripción
Sumario:A convergent, nine‐step (LLS), enantioselective synthesis of α‐cyclopiazonic acid and related natural products is reported. The route features a) an enantioselective aziridination of an imine with a chiral sulfur ylide; b) a bioinspired (3+2)‐cycloaddition of the aziridine onto an alkene; and c) installation of the acetyltetramic acid by an unprecedented tandem carbonylative lactamization/N−O cleavage of a bromoisoxazole.

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