Abstract
Prins cyclization of bis-homoallylic alcohols with aldehydes catalyzed by iron(III) salts shows excellent cis selectivity and yields to form 2,7-disubstituted oxepanes. The iron(III) is able to catalyze this process with unactivated olefins. This cyclization was used as the key step in the shortest total synthesis of (+)-isolaurepan.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alcohols / chemistry
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Aldehydes / chemistry
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Alkenes / chemistry
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Catalysis
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Combinatorial Chemistry Techniques
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Cyclization
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Iron Compounds / chemistry*
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Laurencia / chemistry
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Molecular Structure
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Oxepins / chemical synthesis*
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Oxepins / chemistry
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Stereoisomerism
Substances
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Alcohols
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Aldehydes
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Alkenes
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Iron Compounds
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Oxepins
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isolaurepan