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11-Step Total Synthesis of (-)-Maoecrystal V.

ABSTRACT: An expedient, practical, and enantioselective route to the highly congested ent-kaurane diterpene maoecrystal V is presented. This route, which has been several years in the making, is loosely modeled after a key pinacol shift in the proposed biosynthesis. Only 11 steps, many of which are strategic in that they build key skeletal bonds and incorporate critical functionalities, are required to access (-)-maoecrystal V. Several unique and unexpected maneuvers are featured in this potentially scalable pathway. Reevaluation of the biological activity calls into question the initial exuberance surrounding this natural product.

SUBMITTER: Cernijenko A

PROVIDER: S-EPMC4974602 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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11-Step Total Synthesis of (-)-Maoecrystal V.

Cernijenko Artiom A Risgaard Rune R Baran Phil S PS

Journal of the American Chemical Society 20160726 30

An expedient, practical, and enantioselective route to the highly congested ent-kaurane diterpene maoecrystal V is presented. This route, which has been several years in the making, is loosely modeled after a key pinacol shift in the proposed biosynthesis. Only 11 steps, many of which are strategic in that they build key skeletal bonds and incorporate critical functionalities, are required to access (-)-maoecrystal V. Several unique and unexpected maneuvers are featured in this potentially scala ...[more]

PMID: 27457680

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