Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-cis-Sylvaticin

Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvati...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2009-09, Vol.131 (35), p.12854-12861
Main Authors: Donohoe, Timothy J, Harris, Robert M, Williams, Oliver, Hargaden, Gráinne C, Burrows, Jeremy, Parker, Jeremy
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemistry
Alkenes - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Cyclization
Furans - chemical synthesis
Furans - chemistry
Hydroxylation
Oxidation-Reduction
Stereoisomerism
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Summary:Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja9049959