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Communication | Regular issue | Vol 24, No. 6, 1986, pp.1549-1555
Published online, 1st January, 1970
DOI: 10.3987/R-1986-06-1549
A Synthesis of 4-Cyano-hexahydro-1,5-imino-3-benzazocine-7,10-dione; a Potential Intermediate to Saframycin Synthesis

Hideshi Kurihara, Hiroshi Mishima, and Mamoru Arai*

*Sankyo Research Laboratories, Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan


A simple and efficient synthesis of 4-cyano-1,2,3,4,5,6-hexahydro-1,5-imino-9-methoxy-8-methyl-3-benzazocine-7,10-dione (2a) is described starting from the corresponding lactam (3). Reduction of the lactam (3) with DIBAH followed by oxidation with HNO3 and neutralization of the resulting quinone in the presence of KCN afforded an α-aminonitrile derivative as the single product; the stereochemistry of the introduced cyano group being determined to be α-axial.