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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.

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.

SUBMITTER: Na CG

PROVIDER: S-EPMC9635941 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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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.

Na Christina G CG Kang Suh Hyun SH Sarpong Richmond R

Journal of the American Chemical Society 20221014 42

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 <i>gem</i>-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 isol ...[more]

PMID: 36240482

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