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Synfacts 2006(7): 0636-0636  
DOI: 10.1055/s-2006-941837
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Syntheses of Ophirin B and Astrogorgin

Contributor(s): Philip Kocienski
M. T. Crimmins*, B. H. Brown, H. R. Plake
University of North Carolina, Chapel Hill and Gilead Sciences, Inc., Foster City, USA
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

A ring-closing metathesis was used to construct the oxonene ring first. The oxonene ring then served as a template for a very easy intra­molecular Diels-Alder reaction to generate the hydroisobenzofuran ring system with concomitant creation of four stereogenic centers.