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Total synthesis of vinigrol.

ABSTRACT: The longstanding challenge posed by the complex diterpene vinigrol has been answered for the first time. The notorious difficulty in synthesizing vinigrol stems from its unprecedented decahydro-1,5-butanonaphthalene ring system, eight contiguous stereocenters, and highly congested functionality. This Communication delineates a stereocontrolled 23-step route to vinigrol that is scalable (>5 g prepared of a late-stage intermediate), minimally reliant on protecting group chemistry, and facilitated by a number of unique and chemoselective transformations.

SUBMITTER: Maimone TJ

PROVIDER: S-EPMC2787793 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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Total synthesis of vinigrol.

Maimone Thomas J TJ Shi Jun J Ashida Shinji S Baran Phil S PS

Journal of the American Chemical Society 20091201 47

The longstanding challenge posed by the complex diterpene vinigrol has been answered for the first time. The notorious difficulty in synthesizing vinigrol stems from its unprecedented decahydro-1,5-butanonaphthalene ring system, eight contiguous stereocenters, and highly congested functionality. This Communication delineates a stereocontrolled 23-step route to vinigrol that is scalable (>5 g prepared of a late-stage intermediate), minimally reliant on protecting group chemistry, and facilitated ...[more]

PMID: 19877628

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