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Type: Journal article
Title: Synthesis of the putative structure of tridachiahydropyrone
Author: Jeffery, D.
Perkins, M.
White, J.
Citation: Organic Letters, 2005; 7(8):1581-1584
Publisher: Amer Chemical Soc
Issue Date: 2005
ISSN: 1523-7060
Statement of
David W. Jeffery, Michael V. Perkins, and Jonathan M. White
Abstract: [reaction: see text] A short total synthesis of the putative structure of the marine natural product tridachiahydropyrone as a single enantiomer is described. Novel steps include a cuprate addition and cyclization to form a cyclohexanone ring and formation of the bicyclic pyrone with P(2)O(5) on Celite. The spectroscopic data obtained for compound 1 do not match those reported for tridachiahydropyrone; therefore, revision of the assigned natural product structure is warranted.
Keywords: Animals; Mollusca; Pyrones; Nuclear Magnetic Resonance, Biomolecular; Molecular Structure; Cyclization; Stereoisomerism
Rights: Copyright © 2005 American Chemical Society
RMID: 0020105350
DOI: 10.1021/ol050236d
Appears in Collections:Wine Science publications

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