Total Synthesis of (−)-2-epi-Peloruside A

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 func...

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Bibliographic Details
Published in:Organic letters 2008-12, Vol.10 (24), p.5501-5504
Main Authors: Smith, Amos B, Cox, Jason M, Furuichi, Noriyuki, Kenesky, Craig S, Zheng, Junying, Atasoylu, Onur, Wuest, William M
Format: Article
Language:English
Subjects:
Aldehydes - chemical synthesis
Aldehydes - chemistry
Animals
Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Epoxy Compounds - chemistry
Lactones - chemical synthesis
Lactones - chemistry
Porifera - chemistry
Quinolizines - chemical synthesis
Quinolizines - chemistry
Sulfur Compounds - chemical synthesis
Sulfur Compounds - chemistry
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Summary: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).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol8019132