Total synthesis of the four enantiomerically pure diasteroisomers of the phytoprostanes E1type II and of the 15-E2t-isoprostanes

Journal of Organic Chemistry

Volumn 73, Issue 8, 2008, Pages 3063-3069

  Pinot, Edith ^a   Guy, Alexandre ^a   Fournial, Anais ^a   Balas, Laurence ^a   Rossi, Jean Claude ^a   Durand, Thierry ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOISOMERS; HORNER-WADSWORTH-EMMONS (HWE) COUPLING; ISOPROSTANES; PHYTOPROSTANES;

ENANTIOSELECTIVITY; REACTION KINETICS; STEREOSELECTIVITY;

ISOMERS;

CYCLOPENTENONE DERIVATIVE; ISOPROSTANE DERIVATIVE; PHYTOPROSTANE E1; PROSTANOID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; HORNER REACTION; PLANT PRODUCT; RACEMIC MIXTURE; REACTION ANALYSIS; SYNTHESIS;

CYCLOPENTANES; HYDROGEN; ISOPROSTANES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 42149158973     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702455g     Document Type: Article

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34. We have done Noyori's reduction many times in the past without problems and, as reported in this manuscript, the reduction proceeded well for compounds 20, 25, 35 and only with (S)-BINAL-H for 30 leading to 31a. Astonishingly, we observed a transesterification during the reaction with (R)-BINAL-H with 30 leading to 31b ethyl ester instead of methyl ester. But the difference between a methyl ester and an ethyl ester is not important and 31b was nicely used anyway.