Structure of fredericamycin A, an antitumor antibiotic of a novel skeletal type; spectroscopic and mass spectral characterization

Abstract

IR, UV-visible spectroscopy, circular dichroism, ‘H and 13C NMR studies, high resolution electron impact, field desorption, and fast atom bombardment mass spectral studies are reported for fredericamycin A (NSC-305263), a novel antitumor antibiotic of acid-base indicator type produced by Streptomyces griseus (FCRC-48). The spectral data are cor-related with the structure obtained by X-ray crystallography as (£’,£)-6/,7’-dihydro-4,9,9/-trihydroxy-6-methoxy-3/-(l, 3-pentadienyl)-spiro-[2^T-benz[/]indene-2,8/-[8FI]-cyclopent-D]-isoquinoline]-l,l’,3,5,8(2’#)-pentone. The novel spiro ring antibiotic exhibits unusual LH and 13C NMR spectroscopic and chemical behavior, not previously observed in other anti-biotic structures. © 1987, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved.