Synthesis of the putative structure of tridachiahydropyrone

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2005

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Jeffery, D.
Perkins, M.
White, J.

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Journal article

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Organic Letters, 2005; 7(8):1581-1584

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David W. Jeffery, Michael V. Perkins, and Jonathan M. White

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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.

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Copyright © 2005 American Chemical Society

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