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Synthesis of the Enantiomers of 2-sec-Butyl-4,5-dihydrothiazole and (1R,5S,7R)-3,4-Dehydro-exo-brevicomin, Pheromone Components of the Male Mouse, Mus musculus

✍ Scribed by Takuya Tashiro; Kenji Mori

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 207 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199909)1999:9<2167::aid-ejoc2167>3.0.co;2-l

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✦ Synopsis

Two components [2-sec-butyl-4,5-dihydrothiazole (1) and were obtained with an enantiomeric purity of ca. 92% ee and were found to be readily racemizable. Asymmetric 3,4-dehydro-exo-brevicomin (2)] of a male-produced pheromone of the mouse Mus musculus have been dihydroxylation was employed as the key reaction (15Ǟ16) allowing the preparation of (1R,5S,7R)-2 with ca. 94% ee. synthesized in optically active forms. The enantiomers of 1

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