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Paper | Special issue | Vol 67, No. 2, 2006, pp.597-619
Published online, 8th November, 2005
DOI: 10.3987/COM-05-S(T)18
Improved Syntheses of the FR900482 and Mitomycin Benzazocine Ring Core via Mitsunobu Cyclization

Pascal Ducept, Daniel A. Gubler, and Robert M. Williams*

*Department of Chemistry, Colorado State University, Fort Collins, CO 80523-1872, U.S.A.

Abstract

An asymmetric synthesis of a highly functionalized benzazocine core of FR900482 and the mitomycins has been achieved in 20 and 19 steps, respectively. Key features of the synthesis include a highly chemoselective reduction of a nitro group and a Mitsunobu cyclization using either sulfonamides or carbamates. Removal of the protecting groups afforded the free benzazocine.