Bulletin of the Chemical Society of Japan p. 1273 - 1280 (1988)
Update date:2022-09-26
Topics:
Fujitsawa, Tamotsu
Fujimura, Atsushi
Sato, Toshio
Both enantiomers of various optically pure (R)- and (S)-β-hydroxy esters were generally synthesized from (S)-(p-chlorophenylsulfinyl)acetone obtained by kinetic resolution with bakers' yeast, followed by γ-alkylation, diastereoselective reduction, subsequent introduction of ester group and reductive elimination of the sulfinyl group.The key step of the diastereoselective reduction of (S)-β-keto sulfoxides was performed with diisobutylaluminum hydride to give (R)C-(S)S-β-hydroxy sulfoxides or after complexation with zinc chloride followed by addition of diisobutylaluminum hydride to give (S)C-(S)S-β-hydroxy sulfoxides which were easily separated in an optically pure form by easy crystallization or separation by silica-gel chromatography due to the p-chlorophenyl moiety in the β-hydroxy sulfoxides.The utility of the present method could be successfully demonstrated in the synthesis of both (+)- and (-)-corynomycolic acids from optically pure methyl esters of (R)- and (S)-3-hydroxyoctadecanoic acid by alkylation with tetradecyl iodide at α-position and hydrolysis.
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Doi:10.1007/BF00475336
(1988)Doi:10.1016/S0040-4039(00)82003-1
(1988)Doi:10.1016/0040-4039(88)85189-X
(1988)Doi:10.3762/bjoc.10.81
(2014)Doi:10.1021/acs.joc.6b02106
(2016)Doi:10.1002/ejic.200800146
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