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Synthesis of the Enantiomers of 2‐ sec ‐Butyl‐4,5‐dihydrothiazole and (1 R ,5 S ,7 R )‐3,4‐Dehydro‐ exo ‐brevicomin, Pheromone Components of the Male Mouse, Mus musculus
Author(s) -
Tashiro Takuya,
Mori Kenji
Publication year - 1999
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(199909)1999:9<2167::aid-ejoc2167>3.0.co;2-l
Subject(s) - enantiomer , dihydroxylation , pheromone , stereochemistry , sex pheromone , chemistry , enantioselective synthesis , botany , biology , organic chemistry , catalysis
Two components [2‐ sec ‐butyl‐4,5‐dihydrothiazole ( 1 ) and 3,4‐dehydro‐ exo ‐brevicomin ( 2 )] of a male‐produced pheromone of the mouse Mus musculus have been synthesized in optically active forms. The enantiomers of 1 were obtained with an enantiomeric purity of ca. 92% ee and were found to be readily racemizable. Asymmetric dihydroxylation was employed as the key reaction ( 15 → 16 ) allowing the preparation of (1 R ,5 S ,7 R )‐ 2 with ca. 94% ee .