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Communication | Regular issue | Vol 24, No. 3, 1986, pp.641-645
Published online, 1st January, 1970
DOI: 10.3987/R-1986-03-0641
An Enantioselective Synthesis of (—)-6-Aza-6-carbethoxy-2-oxabicyclo[3.3.0]octan-3-one from S-(—)-Malic Acid

Kozo Shishido, Yuko Sukegawa, Keiichiro Fukumoto,* and Tetsuji Kametani

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

Abstract

An enantioselective synthesis of the title compound, a precursor for the Geissman lactone, from S-(-)-malic acid is described. The synthesis features the diastereoselective intramolecular Michael reaction of the carbamate (3).