Synthesis of Stegobiol and Its Oxidation to Stegobinone, the Components of the Female-Produced Sex Pheromone of the Drugstore Beetle

✍ Scribed by Kenji Mori; Satoshi Sano; Yusuke Yokoyama; Masahiko Bando; Masaru Kido

• Book ID: 102657864
• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 538 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199806)1998:6<1135::aid-ejoc1135>3.0.co;2-k

✦ Synopsis

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-trimethyl-6-(1Ј-methyl-2Ј-oxobutyl)-4H-pyran-4-one (1, Scheme 1) [1] . The minor component of the pheromone was later shown to be stegobiol [2,3-cis-dihydro-2,3,5-trimethyl-6-(2Ј-hydroxy-1Ј-methylbutyl)-4H-pyran-4-one (2)] by Kodama et al. in 1987 [2] . Scheme 1. Structures of the pheromone components of the female drugstore beetle

The unique structure of stegobinone (1) with unkown stereochemistry evoked much interest among synthetic chemists, and the first synthesis of (±)-1 as a mixture of diastereomers at C-1Ј by cyclization of (±)-A (Scheme 2) was reported simultaneously by Mori [3] , Hassner [4] and their respective coworkers in 1979. Subsequently in 1981 Hoffmann et al. cyclized optically active A and separated [᭛]