160204-82-0Relevant articles and documents
Optical resolution of 3-(silyloxy)glutaric acid half esters and their utilization for enantioconvergent synthesis of a HMG-CoA reductase inhibitor
Konoike, Toshiro,Okada, Tetsuo,Araki, Yoshitaka
, p. 3037 - 3040 (2007/10/03)
Useful chiral synthons, (3R)- and (3S)-[(tert- butyldimethylsilyl)oxy]pentanedioic acid monomethyl ester, (R)-1 and (S)-1, were obtained by optical resolution of a racemic mixture of 1. Sulfoxide 8 has been developed from (S)-1 as a new building block for preparing HMG-CoA reductase inhibitors. Two alternate chiral synthons 2 and 8, synthesized from (R)-1 and (S)-1, respectively, were employed for enantioconvergent synthesis of potent inhibitor 15 containing a pyrrole moiety.
Practical synthesis of chiral synthons for the preparation of HMG-CoA reductase inhibitors
Konoike,Araki
, p. 7849 - 7854 (2007/10/02)
A practical procedure for the enantioselective preparation of optically pure (R)- and (S)-monomethyl esters of 3-[(tert-butyldimethylsilyl)oxy]pentanedioic acid has been developed by diastereoselective ring-opening of 3-[(tert-butyldimethylsilyl)oxy]pentanedioic anhydride 5 by benzyl (R)- and (S)-mandelate, respectively. These half-esters afforded chiral Wittig reagent 2 and Horner-Wadsworth-Emmons (HWE) reagent 1 efficiently which have been proved to be useful in the synthesis of HMG-CoA reductase inhibitors. The method is applied to the synthesis of the (R)-3-methylglutaric acid, monomethyl ester.