Abstract
A bioinspired and sustainable procedure for the straightforward synthesis of (±)-aureol has been achieved in eight steps (14% overall yield) from epoxyfarnesol. The key steps are the titanocene(III)-catalyzed radical cascade cyclization of an epoxyfarnesol derivative and a biosynthetically inspired sequence of 1,2-hydride and methyl shifts.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Biochemical Phenomena
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Catalysis
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Cyclization
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Epoxy Compounds / chemistry*
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Farnesol / chemistry*
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Molecular Structure
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Organometallic Compounds / chemistry*
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Sesquiterpenes / chemical synthesis*
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Sesquiterpenes / chemistry
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Stereoisomerism
Substances
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Epoxy Compounds
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Organometallic Compounds
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Sesquiterpenes
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aureol
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titanocene
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Farnesol