Abstract
A convergent synthesis of the marine natural product (+)-peloruside has been reported. This target has been assembled through the successive application of two methyl ketone boron aldol addition reactions to the latent C(7)-C(11) dialdehyde synthon. This approach afforded a 22-step synthesis of this natural product. The influence of resident stereocenters on aldol reaction diastereoselection has been examined in detail.
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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Alcohols
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Aldehydes
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Animals
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Biological Products / chemical synthesis
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
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Lactones / chemical synthesis*
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Porifera / chemistry
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Stereoisomerism
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Tubulin Modulators / chemical synthesis
Substances
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Alcohols
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Aldehydes
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Biological Products
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Bridged Bicyclo Compounds, Heterocyclic
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Lactones
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Tubulin Modulators
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peloruside A