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A synthesis of (−)-sitophilate by utilizing yeast-mediated reduction of an enol ester

✍ Scribed by Takeshi Sugai; Daisuke Sakuma; Naoki Kobayashi; Hiromichi Ohta

Book ID
104204902
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
489 KB
Volume
47
Category
Article
ISSN
0040-4020

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✦ Synopsis

The mrcrobral reduchon of l'-ethylpropyl 2-methyl-3-oxopentanoate, a j3-keto ester possessmg bulky subsutuent, as well as the cormspondmg enol ester was exammed Eprmenc nuxture of hydroxy ester, contammg (2S.3.Qisomer as the major product (9296e e ,43%d e ) was obtamed via the reducuon of enol ester wrth growing cells of Ptchta farmosa IAM 4682 in 63% yreld The resulting p-hydroxy ester was converted to (2$3R)-isomer (889be e ,96%d e ). of which e e was further enhanced by the hpase-catalyzed partial hydrolysis of the correspondmg chloroacetate to give (-)-ntophllate, (998e e , 98%d e ) an aggregauon pheromone of Suophrllus granarlus L

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