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Paper | Regular issue | Vol 51, No. 10, 1999, pp.2415-2421
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8643
Convenient Synthesis of Cyclohexa[a]pyrrolo[2,1-b][3]benzazepine, a Cephalotaxus Alkaloid Analogue

Hitoshi Tanaka,* Mitsunobu Doi, Hiroshi Shimizu, and Hideo Etoh

*Faculty of Pharmacy, Meijo University, 150 Yagoto, Tempaku-ku, Nagoya, Aichi 468-8503, Japan

Abstract

Irradiation of N-(3-hydroxy-4-methoxyphenethyl)-3-(2-iodo-5-methoxyphenyl)propionamide (11) in methanol in the presence of sodium hydroxide furnished 3-hydroxy-2,12-dimethoxy-6,7,9,10-tetrahydrodibenz-[d,f]azecin-8(5H)-one (14) which was successfully led to cephalotaxine analogue (17) bearing pyrrolo[2,1-b][3]benzazepine skeleton by reduction with borane followed by Birch reduction and subsequent acidic treatment. The structure of 17 was established by means of X-ray crystallography.