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Development of a C–C Bond Cleavage/Vinylation/Mizoroki–Heck Cascade Reaction: Application to the Total Synthesis of 14- and 15-Hydroxypatchoulol

Published Web Location

https://doi.org/10.1021/jacs.2c09201
Abstract

A C-C bond cleavage/vinylation/Mizoroki-Heck cascade reaction has been developed to provide access to densely functionalized bicyclo[2.2.2]octane frameworks. The sequence proceeds through the coupling of dihydroxylated pinene derivatives, prepared from carvone, with gem-dichloroalkenes. The method was applied to 12-step total syntheses of both 14- and 15-hydroxypatchoulol, which provided unambiguous support for the structure of the natural products and corrects a misassignment in the isolation report.

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