Abstract
An enantioselective synthesis of the ABC-tricyclic furanochroman core of phomactin A has been accomplished by a γ-hydroxylation approach. The C ring was established by γ-hydroxylation of an α-enone. The regioselectivity was optimized by using a strong base with an oxophilic cation (t-BuLi) and a bulky oxygen donor (Davis reagent), which afforded the γ-hydroxylation product selectively in 63% yield.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Ascomycota / chemistry
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Chromans / chemical synthesis
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Chromans / chemistry
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Furans / chemical synthesis
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Furans / chemistry
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Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Hydroxylation
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Indicators and Reagents
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Molecular Structure
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Stereoisomerism
Substances
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Chromans
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Furans
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Heterocyclic Compounds, 4 or More Rings
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Indicators and Reagents
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furanochroman
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phomactin A