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Paper | Special issue | Vol 76, No. 1, 2008, pp.521-539
Published online, 17th April, 2008
DOI: 10.3987/COM-08-S(N)40
Total Synthesis of Isoindolobenzazepine Alkaloids, Lennoxamine and Chilenine, Based on Palladium-Catalyzed Reduction of Alkenyl Phosphates

Haruhiko Fuwa* and Makoto Sasaki*

*Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, 1-1 Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan

Abstract

An efficient method for the synthesis of enol ethers and enecarbamates has been developed based on palladium(0)-catalyzed chemoselective reduction of alkenyl phosphates. This method has been applied successfully to the total synthesis of two isoindolobenzazepine alkaloids, lennoxamine and chilenine.