Abstract
An improved methodology for the preparation of enantiopure oxabicyclo[3.2.1]octadienes via a stereodivergent resolution is reported. High catalyst control proximal to the oxabridged stereocenter produces readily separable diastereomers in high yield (>92%) and with excellent optical purity (>95% ee). This resolution strategy is amenable to large-scale preparations, and the utility of the resolution was further demonstrated in the asymmetric preparation of a key intermediate used in the synthesis of the antibiotic (-)-platensimycin.
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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Adamantane / chemical synthesis*
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Adamantane / chemistry
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Aminobenzoates / chemical synthesis*
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Aminobenzoates / chemistry
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Anilides / chemical synthesis*
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Anilides / chemistry
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Biological Products / chemistry*
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Bridged Bicyclo Compounds / chemistry*
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Ketones / chemistry*
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Molecular Structure
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Stereoisomerism
Substances
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Aminobenzoates
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Anilides
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Biological Products
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Bridged Bicyclo Compounds
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Ketones
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Adamantane
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platensimycin