An efficient chemical conversion of mitomycin A to isomitomycin A

…, M Kono, S Ikeda, N Yoda, N Hirayama

Index: Kasai; Kono; Ikeda; Yoda; Hirayama Journal of Organic Chemistry, 1992 , vol. 57, # 26 p. 7296 - 7299

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Citation Number: 10

Abstract

After inspection of the X-ray crystallographic anal-of mitomycin A (la) and albomitomycin A (2), an efficient chemical conversion of la to isomitomycin A (3) via 2 was accomplished in 68% overall yield. First, la was converted to (8aS)-8a-bromoalbomitomycin A (4b) in 89% yield, which was reduced with tributyltin hydride and AIBN to give 2 in 85% yield. Second, the C4a-N4 bond of 2 was selectively cleaved under hydrogenolysis conditions, and ...