A short synthesis of (−)-(4 R,5 S)-sitophilure using the regio- and stereoselective reduction of 3-acyltetrahydrothiopyran-4-ones with baker's yeast

A short synthesis of (−)-(4 R,5 S)-sitophilure using the regio- and stereoselective reduction of 3-acyltetrahydrothiopyran-4-ones with baker's yeast

Bakers' yeast reduction of 3-acyltetrahydrothiopyran-4-ones is regio- and enantioselective, yielding predominantly (3 R,4 S)-3-acyl-4- hydroxytetrahydrothiopyranes with high optical purity. This reduction method coupled with the Raney-nickel desulfurization provides a ready access to the rice a...

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Veröffentlicht in:Tetrahedron letters 1992-01, Vol.33 (38), p.5567-5570
Hauptverfasser: Fujisawa, Tamotsu, Mobele, Bingidimi I., Shimizu, Makoto
Format: Artikel
Sprache:eng
Schlagworte:
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Fundamental and applied biological sciences. Psychology
Methods. Procedures. Technologies
Saccharomyces cerevisiae
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Zusammenfassung:Bakers' yeast reduction of 3-acyltetrahydrothiopyran-4-ones is regio- and enantioselective, yielding predominantly (3 R,4 S)-3-acyl-4- hydroxytetrahydrothiopyranes with high optical purity. This reduction method coupled with the Raney-nickel desulfurization provides a ready access to the rice and maize weevils aggregation pheromone, (−)-(4 R,5 S)-sitophilure, in high optical purity. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)61147-4