Abstract
An efficient synthesis of antitumor marine natural product (+)-pericosine A was achieved from (-)-quinic acid in 11.7% overall yield, which is 20 times better than our previously reported synthesis. The crucial steps of this synthesis include the regio- and stereoselective bromohydrination of an unstable diene and the ring opening of an epoxide. This synthetic route was applicable to a synthesis of (+)-pericosine C and also to a synthesis of (-)-pericosine C.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Carbasugars / chemical synthesis*
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Carbasugars / chemistry
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Catalysis
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Epoxy Compounds / chemical synthesis*
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Epoxy Compounds / chemistry
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Molecular Structure
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Molybdenum / chemistry*
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Phosphoric Acids / chemistry*
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Shikimic Acid / analogs & derivatives*
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Shikimic Acid / chemical synthesis
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Shikimic Acid / chemistry
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Stereoisomerism
Substances
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Carbasugars
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Epoxy Compounds
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Phosphoric Acids
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methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate
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pericosine C
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Shikimic Acid
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Molybdenum
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phosphomolybdic acid