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Synthesis of Stegobiol and Its Oxidation to Stegobinone, the Components of the Female‐Produced Sex Pheromone of the Drugstore Beetle
Author(s) -
Mori Kenji,
Sano Satoshi,
Yokoyama Yusuke,
Bando Masahiko,
Kido Masaru
Publication year - 1998
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/(sici)1099-0690(199806)1998:6<1135::aid-ejoc1135>3.0.co;2-k
Subject(s) - chemistry , reagent , ruthenium , pheromone , pyran , chromic acid , organic chemistry , stereochemistry , sex pheromone , catalysis , botany , biology
Abstract Crystalline (–)‐stegobinone [(2 S ,3 R ,1′ R )]‐2,3‐dihydro‐2,3,5‐trimethyl‐6‐(1′‐methyl‐2′‐oxobutyl)‐4 H ‐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 [(2 S ,3 R ,1′ S ,2′ S )‐2,3‐dihydro‐2,3,5‐trimethyl‐6‐(2′‐hydroxy‐1′‐methylbutyl)‐4 H ‐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.