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Paper | Regular issue | Vol 51, No. 6, 1999, pp.1321-1343
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8494
2(3H)- and 2(5H)-Furanones. VII. Chirality Transfer on the Tetronic Acid Templates

Takefumi Momose, Naoki Toyooka,* Morihiro Nishio, Hiroyuki Shinoda, Hiromi Fujii, and Hironobu Yanagino

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan

Abstract

The chirality transfer on the β-tetronic acid templates has been examined via highly diastereoselective alkylation or the Michael reaction at the α-position of the acids. Synthetic utility of this transfer procedure was demonstrated by the formal synthesis of (+)-cassiol and enantiodivergent synthesis of O-methyljoubertiamine.