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

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Abstract
IR, UV-visible spectroscopy, circular dichroism, 1H 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 antiobiotic of acid-base indicator type produced by Streptomyces griseus (FCRC-48). The spectral data are correlated with the structure obtained by X-ray crystallography as (E,E)-6'',7''-dihydro-4,9,9''-trihydroxy-6-methoxy-3''-(1,3-pentadienyl)-spiro-[2H-benz[f]indene-2,8''-[8H]-cyclopent-[g]-isoquinoline]-1,1'',3,5,8(2''H)-pentone. The novel spiro ring antibiotic exhibits unusual 1H and 13C NMR spectroscopic and chemical behavior, not previously observed in other antibiotic structures.