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Synfacts 2008(5): 0441-0441  
DOI: 10.1055/s-2008-1072711
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Thromboxane B2

Contributor(s): Philip Kocienski, Zofia Komsta
C. C. Marvin, A. J. L. Clemens, S. D. Burke*
University of Wisconsin-Madison, USA
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Publication History

Publication Date:
23 April 2008 (online)

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Significance

Thromboxane B2 (TXB2) is a stable metabolite formed from thromboxane A2 (TXA2) and a major product following blood platelet aggregation. The most interesting part of the synthesis is the formation of the bicyclic acetal in D through intermolecular ketalization followed by ring-closing metathesis. The known intermediate I was subjected to the previously published three-step sequence (N. A. Nelson, R. W. Jackson Tetrahedron Lett. 1976, 17, 3275), to give the target material.