Journal
TETRAHEDRON
Volume 67, Issue 34, Pages 6300-6307Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.06.015
Keywords
Antifungal; Natural products; Enantioselective; Synthesis
Categories
Funding
- University of Milan
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An enantioselective synthesis of the structure reported for the natural antifungal compound, (-)-crassinervic acid (1), has been achieved starting from geraniol and p-hydroxybenzoic acid. The key chirality-inducing step is a Sharpless asymmetric epoxidation of an allylic alcohol, on the basis of which the S configuration can be assigned to the (-) natural enantiomer. The discrepancies between the spectroscopic data for synthetic and natural crassinervic acid cast some doubts on the structure assigned to the natural compound. A possible revised structure is discussed. (C) 2011 Elsevier Ltd. All rights reserved.
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