Studies Related to Antitumor Antibiotics. Part III. Syntheses of 1,2,3,4,5,6-Hexahydro-2,3-benzazocin-5-ones as Possible Intermediates in the Biosynthesis of Mitomycins

Abstract

The synthesis of 8-methoxy-9-methyl-N-p-toluenesulfonyl-1,2,3,4,5,6-hexahydro-2,3-benzazocin-5-one (23) and its conversion via transannular interaction to the 2,3-dihydro-lH-pyrrolo[1,2-a]indole ABC parent ring system of the antitumor antibiotic mitomycin C is described. The possible implication of this result in the biosynthesis of the mitosanes and the connection with the structurally and pharmacologically related pyrrolizidine alkaloids is discussed.