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Synfacts 2005(0): 0001-0001  
DOI: 10.1055/s-2005-865341
Synthesis of Natural Products and Drugs
© Georg Thieme Verlag Stuttgart · New York

Catalytic Asymmetric Synthesis of Apple Leafminer Pheromones

Contributor(s): Philip Kocienski
R. P. Van Summeren, S. J. W. Reijmer, B. L. Feringa*, A. J. Minaard
University of Groningen, The Netherlands
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Publikationsdatum:
20. Juli 2005 (online)

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Significance

Starting from cycloocta-2,7-dienone, all four diastereoisomeric 8-hydroxy-3,7-dimethyloctanoic acids were prepared in four steps (38% overall) and one of them (B) was transformed to pheromones C and D of the apple leafminer (Lyonetia prunifoliella) in a further four steps. A new method for the desymmetrization of cross-conjugated dienones is presented.