Abstract
Two types of trans-THF cores, present in acetogenins, have been synthesized by an intramolecular iodoetherification reaction. The starting alkenol was obtained in a few steps from a chiral cis-diol resulting from microbial oxidation of bromobenzene. The cyclization gave complete stereoselectivity for trans-THF cores with either (S,S) or (R,R) configurations at the THF chiral carbons.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetogenins / chemical synthesis*
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Acetogenins / chemistry
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Alcohols / chemistry
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Annonaceae / chemistry
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Bromobenzenes / chemistry*
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Cyclization
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Furans / chemical synthesis*
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Furans / chemistry
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Molecular Structure
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Oxidation-Reduction
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Acetogenins
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Alcohols
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Bromobenzenes
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Furans
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tetrahydrofuran