Abstract
[reaction: see text] The callipeltoside A chlorocyclopropyl-containing dienyne side chain has been synthesized in nine steps and 33% overall yield from commercially available 1,2,5,6-O-dicyclohexylidene-D-mannitol. The key steps in the synthesis are a highly diastereoselective cyclopropanation of a vinyl chloride allylic ether and a Suzuki cross-coupling to complete the carbon framework.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Anti-Bacterial Agents / chemical synthesis*
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Cyclopropanes / chemical synthesis*
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Macrolides*
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Mannitol / analogs & derivatives
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Mannitol / chemistry
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Molecular Structure
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Stereoisomerism
Substances
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1,2,5,6-O-dicyclohexylidenemannitol
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Anti-Bacterial Agents
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Cyclopropanes
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Macrolides
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callipeltoside A
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Mannitol