Synthesis of cis-Solamin

H. Göksel; C. B. W. Stark

doi:10.1055/s-2006-955648

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Synfacts 2007(1): 0012-0012
DOI: 10.1055/s-2006-955648

Synthesis of Natural Products and Potential Drugs

Synthesis of cis-Solamin

Contributor(s): Philip Kocienski, Thomas Snaddon
H. Göksel, C. B. W. Stark*
Freie Universität Berlin, Germany

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Publication History

Publication Date:
15 December 2006 (online)

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Significance

This synthesis of the acetogenin cis-solamin is noteworthy for (1) the preparation of the tetrahydrofuran core by a RuO₄-catalyzed oxidative cyclization reaction, and (2) the enzymatic desymmetrization of meso-tetrahydrofuran D. For an alternative synthesis of cis-solamin employing an oxidative diene cyclization and a ruthenium-catalyzed Alder-ene reaction, see: A. R. L. Cecil, R. C. D. Brown Org. Lett. 2002, 4, 3715-3718 and A. R. L. Cecil, Y. L. Hu, M. J. Vicent, R. Duncan, R. C. D. Brown J. Org. Chem. 2004, 69, 3368-3374.