C-C 键断裂/乙烯基化/Mizoroki-Heck 级联反应的开发：在 14-和 15-羟基岩兰醇全合成中的应用。
Development of a C-C Bond Cleavage/Vinylation/Mizoroki-Heck Cascade Reaction: Application to the Total Synthesis of 14- and 15-Hydroxypatchoulol.
机构信息
Department of Chemistry, University of California, Berkeley, California 94720, United States.
出版信息
J Am Chem Soc. 2022 Oct 26;144(42):19253-19257. doi: 10.1021/jacs.2c09201. Epub 2022 Oct 14.
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 -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.
摘要
发展了 C-C 键断裂/乙烯基化/Mizoroki-Heck 级联反应，以提供获得稠合官能化双环[2.2.2]辛烷骨架的途径。该序列通过与二氯代烯烃的耦合进行，所述二氯代烯烃由香芹酮制备得到。该方法应用于 14-和 15-羟基对盖醇的 12 步全合成，为天然产物的结构提供了明确的支持，并纠正了分离报告中的错误分配。
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