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Note | Regular issue | Vol 63, No. 1, 2004, pp.137-143
Published online, 31st October, 2003
DOI: 10.3987/COM-03-9919
Preparation and Optical Resolution of a New Helical Lactone Carrying the 2,8-Dioxabicyclo[3.3.0]octane Ring System

Makoto Yamaye,* Yusuke Ikeda, Namiko Cho(Toh), Yoshinori Miura, Tetsutaro Yoshinaga, Katsuya Mukae, and Toshiaki Tsuru

*Faculty of Engineering, Kyushu Kyoritsu University, 1-8 Jiyugaoka, Yahatanishiku, Kitakyushu 807-8585, Japan

Abstract

A new overcrowded lactone (3) carrying the 2,8-dioxabicyclo[3.3.0]octane ring system was prepared by a simple treatment of tetraol (1) (prepared from 2,7-dihydroxynaphthalene and glyoxal) with 3,5-xylenol, and readily resolved into its enantiomers having a specific rotation of >800° (absolute value). A preliminary experiment demonstrated that 3 would be a promising resolving agent.