期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 144, 期 42, 页码 19253-19257出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c09201
关键词
-
资金
- National Institutes of General Medical Sciences [R35 GM130345]
- NIH [F32 GM137490, S10OD024998]
A C-C bond cleavage/vinylation/Mizoroki-Heck cascade reaction has been developed to access densely functionalized bicyclo[2.2.2]octane frameworks. The method was successfully applied in the total synthesis of 14- and 15-hydroxypatchoulol, providing unambiguous support for their structures and correcting a misassignment in the isolation report.
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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