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Communication | Special issue | Vol 74, No. 1, 2007, pp.159-166
Published online, 19th October, 2007
DOI: 10.3987/COM-07-S(W)28
Synthesis of a Series of Structural Analogues of the Cinchona Alkaloids

Kadzushi Furukawa, Masahiro Katsukawa, Mohammad Nuruzzaman, and Yuichi Kobayashi*

*Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan

Abstract

Five olefins, each possessing an aryl (Ar) group, an aliphatic moiety, and a protected amino group as N-Teoc (-CO2(CH2)2TMS) or N3 at the aliphatic end, were converted to the corresponding epoxides with high ee. The amino group was generated by deprotection of the N-Teoc group with CsF or by Staudinger reaction of the azide group at elevated temperatures, under which the intramolecular epoxide ring-opening with the resulting amino group took place concomitantly to afford the analogues of the Cinchona alkaloids.