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Synfacts 2005(0): 0007-0007  
DOI: 10.1055/s-2005-865350
Synthesis of Natural Products and Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (-)-Minovine

Contributor(s): Philip Kocienski
Z. Q. Yuan, H. Ishikawa, D. L. Boger*
The Scripps Research Institute, La Jolla, USA
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Publication History

Publication Date:
20 July 2005 (online)

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Significance

Three rings in the target molecule together with five stereogenic centers were created in a single operation by heating the 1,3,4-oxadiazole A in 1,2-dichlorobenzene. Three tandem pericyclic processes were involved: a Diels-Alder reaction to form B, a retro [3+2] reaction to form dipole C, and a dipolar cycloaddition to form D in 74% yield.