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Communication | Regular issue | Vol 14, No. 8, 1980, pp.1097-1100
Published online, 1st January, 1970
DOI: 10.3987/R-1980-08-1097
A Modified Total Synthesis of (±)-Lycorine

T. Sano,* N. Kashiwaba, J. Toda, Y. Tsuda, and H. Irie

*Showa Pharmaceutical University, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan

Abstract

A modified total synthesis of lycorine was accomplished starting from the lactam-ester (5). Selective reduction of the lactam carbonyl of 5, followed by cyclization gave 5-oxolycorene (4). Epoxidation of 4 gave stereoselectively the α-epoxide (9). Repeated application of Sharpless method to convert epoxide into allylic alcohol and acetylation of the product gave diacetyl 5-oxolycorine (19). Lithium aluminium hydride reduction of 19 gave (±)-lycorine.