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Chemoenzymatic Synthesis of Stegobinone and Stegobiol, Components of the Natural Sex Pheromone of the Drugstore Beetle ( Stegobium paniceum L. )
Author(s) -
Kalaitzakis Dimitris,
Smonou Ioulia
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101319
Subject(s) - chemistry , stereoselectivity , sex pheromone , enantioselective synthesis , pheromone , stereochemistry , diketone , enzyme , organic chemistry , botany , catalysis , biology
NADPH‐dependent ketoreductases were used for the chemoenzymatic stereoselective synthesis of the two componentsof the natural sex pheromone of the drugstore beetle. The key step in the asymmetric synthesis was the enzymatic reduction of an α‐methyl‐1,3‐diketone and an α‐methyl‐β‐keto ester, which finally led to the preparation of crystalline stegobinone and stegobiol.