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Synfacts 2008(11): 1138-1138  
DOI: 10.1055/s-0028-1083413
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Hirsutene

Contributor(s): Philip Kocienski, Arndt W. Schmidt
C. L. Chandler, B. List*
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
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Publication History

Publication Date:
23 October 2008 (online)

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Significance

Screening of 4-substituted prolines revealed that trans-4-fluoroproline efficiently catalyzes transannular aldolizations of cycloalkandiones. The generality of this unprecedented reaction was demonstrated by the synthesis of a variety of bi- and tricyclic compounds in high yield and enantioselectivity. The new concept was then applied to the total synthesis of (+)-hirsutene.