110996-50-4Relevant articles and documents
Chemoenzymatic synthesis of stegobinone and stegobiol, components of the natural sex pheromone of the drugstore beetle (Stegobium paniceum L.)
Kalaitzakis, Dimitris,Smonou, Ioulia
, p. 43 - 46 (2012/02/14)
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-di
Synthesis of stegobiol and its oxidation to stegobinone, the components of the female-produced sex pheromone of the drugstore beetle
Mori, Kenji,Sano, Satoshi,Yokoyama, Yusuke,Bando, Masahiko,Kido, Masaru
, p. 1135 - 1141 (2007/10/03)
Crystalline (-)-stegobinone [(2S,3R,1′R)]-2,3-dihydro-2,3,5-trimethyl-6-(1′-methyl-2′- oxobutyl)-4H-pyran-4-one (1)], the major component of the female-produced sex pheromone of the drugstore beetle (Stegobium paniceum L.), was synthesized by oxidation of crystalline and the minor component (-)-stegobiol [(2S,3R,1′S,2′S)-2,3-dihydro-2,3,5-trimethyl-6-(2′-hydroxy- 1′-methylbutyl)-4H-pyran-4-one (2)] under the appropriate conditions using Jones's chromic acid, Dess-Martin's periodinane or Ley's ruthenium reagent. The latter (2) was synthesized by employing lipase and the Sharpless epoxidation for the introduction of the proper chiral centers. The streostructure of 1 was comfirmed by X-ray analysis.
High-Precision Asymmetric Synthesis of Stegobiol and Stegobinone via Boronic Esters
Matteson, Donald S.,Man, Hon-Wah
, p. 6545 - 6547 (2007/10/02)
Highly stereoselective boronic ester chemistry has been used to synthesize the drugstore beetle pheromones stegobiol and stegobinone.The convergent route utilizes a single intermediate containing all of the stereogenic centers for both segments of the phe
