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Total synthesis of (-)-2-epi-peloruside A.

ABSTRACT: A convergent synthesis of (-)-2-epi-peloruside A has been achieved. Highlights include implementation of multicomponent type I anion relay chemistry (ARC) to unite 2-TBS-1,3-dithiane with two epoxides to construct the eastern hemisphere, a late-stage dithiane union to secure the complete, fully functionalized carbon backbone, and Yamaguchi macrolactonization, which led to (-)-2-epi-peloruside A via an unexpected epimerization at C(2).

SUBMITTER: Smith AB

PROVIDER: S-EPMC2697658 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Total synthesis of (-)-2-epi-peloruside A.

Smith Amos B AB Cox Jason M JM Furuichi Noriyuki N Kenesky Craig S CS Zheng Junying J Atasoylu Onur O Wuest William M WM

Organic letters 20081201 24

A convergent synthesis of (-)-2-epi-peloruside A has been achieved. Highlights include implementation of multicomponent type I anion relay chemistry (ARC) to unite 2-TBS-1,3-dithiane with two epoxides to construct the eastern hemisphere, a late-stage dithiane union to secure the complete, fully functionalized carbon backbone, and Yamaguchi macrolactonization, which led to (-)-2-epi-peloruside A via an unexpected epimerization at C(2). ...[more]

PMID: 19007239

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