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Communication | Regular issue | Vol 31, No. 7, 1990, pp.1237-1240
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5439
A Novel Appraoch to Chiral Cyclobutanes — An Enantioselective Total Synthesis of (+)-(S,Z)-5-(1-Decenyl)dihydro-2(3H)-furanone and (-)-(R,Z)-5-(1-Decenyl)dihydro-2(3H)-furanone

Hideo Nemoto, Hiroki Ishibashi, Masahiko Mori, Shigekazu Fujita, and Keiichiro Fukumoto*

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


An enantioselective synthesis of (+)-(S,Z)-5-(1-decenyl)dihydro-2(3H)-furanone (25) and (-)-(R,Z)-5-(1-decenyl)dihydro-2(3H)-furanone (26) was achieved starting with either (10) or (11) prepared by reduction of the chiral cyclobutanone (8) which was derived stereospecifically from the cyclopropyl carbinol (6) by ring expansion reaction.