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Communication | Regular issue | Vol 16, No. 9, 1981, pp.1509-1513
Published online, 1st January, 1970
DOI: 10.3987/R-1981-09-1509
Synthesis of Methyl 3(R)-Methyl-5-oxopentanoate, a Potential Chiral Synthon for Versatile Natural Products, from Common Chiral Intermediates

Seiichi Takano,* Ken’ichi Masuda, and Kunio Ogasawara

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Conversion of both 3(R)-methylcyclopentanone (4) and ι-menthone (8) into methyl 3(R)-methyl-5-oxopentanoate (7) and its derivatives through a α-diketone monothioketal intermediate has been achieved. Using these chiral products as common synthons, an enantioselective route to rose oxide[(4R)-(21)] and its enantiomer[(4S)- (21)] has been developed.