Abstract
[reaction: see text] A stereoselective synthesis of (-)-ilimaquinone (4) is presented. The synthetic strategy is based on a novel radical decarboxylation and quinone addition methodology that produces quinone 7 from reaction of thiohydroxamic acid derivative 8 with benzoquinone (9). Final functionalization of 7 to ilimaquinone (4) is achieved by exploring the electronic effects of the residual thiopyridyl group.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Animals
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Anti-HIV Agents / chemical synthesis
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Anti-Inflammatory Agents / chemical synthesis
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Antineoplastic Agents / chemical synthesis
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Porifera / chemistry
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Quinones / chemical synthesis*
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Quinones / chemistry
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Sesquiterpenes / chemical synthesis*
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Sesquiterpenes / chemistry
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Stereoisomerism
Substances
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Anti-HIV Agents
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Anti-Inflammatory Agents
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Antineoplastic Agents
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Quinones
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Sesquiterpenes
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ilimaquinone