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Report | Regular issue | Vol 22, No. 3, 1984, pp.569-579
Published online, 1st January, 1970
DOI: 10.3987/R-1984-03-0569
Aziridine in Alkaloid Synthesis. VI. Alternative Synthetic Approach to the Basic Skeleton of Erythrina Alkaloids

Tetsuji Kametani,* Kimio Higashiyama, Yoshio Honda, and Hirotaka Otomatsu

*Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

Treatment of the aziridine (2) with 3-bromocyclohex-2-en-1-one afforded the bromo derivative (4), which was then thermally cyclized to give the enaminone (8) siteselectively. Reaction of 10 with mercuric acetate furnished 12 instead of the desired erythrinan-type compound, whereas the acid-catalyzed cyclizetion of 8 yielded the desired cyclized product (14).