Chicamycin, a new antitumor antibiotic. II. Structure determination of chicamycins A and B.

Abstract
Structures of chicamycins A and B were determined from a series of chemical degradation studies coupled with spectroscopic analysis. Chicamycin A is 2(S),11(R),11a(S)-1,2,3,10,11,11a-hexahydro-2,8-dihydroxy-7,11-dimethoxy-5H-pyrrolo-[2,1-c][1,4]-benzodiazepin-5-one. Chicamycin B is 2(S),11a(S)-1,2,3,11a-tetrahydro-2,8-dihydroxy-7-methoxy-5H-pyrrolo-[2,1-c][1,4]-benzodiazepin-5-one, which is the demethanol form of chicamycin A. The structure of chicamycin B is closely related to that of neothramycin, differing only in the position of a hydroxyl substituent on the pyrrolidine ring.

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