Abstract
The first total synthesis of the natural product (3S,7R)-5,6-dehydro-de-O-methyl centrolobine and various analogues is reported, using a highly regio- and diastereoselective Mizoroki-Heck reaction of phenol diazonium salts and enantiopure dihydropyrans. The assigned relative configuration was confirmed by single-crystal X-ray structure analysis, but a revision of the absolute configuration is proposed based on polarimetric measurement.
© 2011 American Chemical Society
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Biological Products / chemical synthesis
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Biological Products / chemistry
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Catalysis
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Diarylheptanoids / chemical synthesis*
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Diarylheptanoids / chemistry
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Diazonium Compounds / chemistry*
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Ethers, Cyclic / chemistry
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Palladium / chemistry*
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Phenol / chemistry*
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Pyrans / chemical synthesis
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Pyrans / chemistry
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Stereoisomerism
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Substrate Specificity
Substances
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Biological Products
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Diarylheptanoids
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Diazonium Compounds
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Ethers, Cyclic
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Pyrans
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centrolobin
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Phenol
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Palladium