Development of a C-C Bond Cleavage/Vinylation/Mizoroki-Heck Cascade Reaction: Application to the Total Synthesis of 14- and 15-Hydroxypatchoulol.
J Am Chem Soc
; 144(42): 19253-19257, 2022 10 26.
Article
em En
| MEDLINE
| ID: mdl-36240482
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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MEDLINE
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Produtos Biológicos
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Octanos
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En
Ano de publicação:
2022
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Article