Asymmetric synthesis of the δ-lactone moiety in mevinic acid derivatives using an enzymatic procedure

Asymmetric induction into meso-1,3-diacetoxy-5-cycloheptene 4 by PFL-catalyzed hydrolysis afforded monoacetate (1S,3R)- 5 of 96% enantiomeric excess (e.e), which was converted into a synthetic equivalent 14 of the δ-lactone moiety in mevinic acid derivatives. Asymmetric induction into meso-1,3-diace...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 8; no. 2; pp. 195 - 201
Main Authors Kaku, Hidetaka, Tanaka, Masakazu, Norimine, Yoshihiko, Miyashita, Yuko, Suemune, Hiroshi, Sakai, Kiyoshi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.01.1997
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
HMG-COA REDUCTASE
ML-236B
INHIBITORS
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Summary:Asymmetric induction into meso-1,3-diacetoxy-5-cycloheptene 4 by PFL-catalyzed hydrolysis afforded monoacetate (1S,3R)- 5 of 96% enantiomeric excess (e.e), which was converted into a synthetic equivalent 14 of the δ-lactone moiety in mevinic acid derivatives. Asymmetric induction into meso-1,3-diacetoxy-5-cycloheptene by PFL-catalyzed hydrolysis afforded (1 S,3 R)-monoacetate of 96 %ee, which was converted into a synthetic equivalent of the δ-lactone moiety in mevinic acid derivatives.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(96)00508-3