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).
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Aldehydes / chemical synthesis*
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Aldehydes / chemistry
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Animals
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
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Bridged Bicyclo Compounds, Heterocyclic / chemistry
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Epoxy Compounds / chemistry
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Lactones / chemical synthesis*
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Lactones / chemistry
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Porifera / chemistry
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Quinolizines / chemical synthesis*
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Quinolizines / chemistry
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Sulfur Compounds / chemical synthesis*
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Sulfur Compounds / chemistry
Substances
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Aldehydes
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Bridged Bicyclo Compounds, Heterocyclic
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Epoxy Compounds
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Lactones
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Quinolizines
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Sulfur Compounds
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dithiane
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peloruside A