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Chemoenzymatic Synthesis of Stegobinone and Stegobiol, Components of the Natural Sex Pheromone of the Drugstore Beetle (Stegobium paniceum L.)

✍ Scribed by Dimitris Kalaitzakis; Ioulia Smonou

Book ID
102172300
Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
274 KB
Volume
2012
Category
Article
ISSN
1434-193X

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Drugstore beetle (Stegobium paniceum L.) is a serious pest of a wide variety of commodities and stored products. In 1978 Y. Kuwahara et al. proposed the structure of stegobinone, the major and crystalline component of the femaleproduced sex pheromone of S. paniceum, as 2,3-cis-dihydro-2,3,5-trimethy

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C-3 took place to some extent. The crude 2 was oxidized under the Swern condition to give (2S,3IZ,l'R)-stegobinone 1 in 14.0 % yield from 3 after purification by prep TLC. The unwanted by-product, (2S,3S,l'R)-stegobinone, could be removed by TLC separation. The IR and mass spectral properties of our