Synthesis of adriamycin and 7,9-epiadriamycin

Details Synthesis of adriamycin and 7,9-epiadriamycin Synthesis of adriamycin and 7,9-epiadriamycin

1976-01-15

1977-03-15

Helfin, Bernard

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260465F, 260473F, 2603459, 260487, C07C 4982

Patent

active

040124487

ABSTRACT:
A process for the synthesis of adriamycin and 7,9-epiadriamycin, both active antineoplastic agents, in which 7-deoxydaunomycinone, in either the 9s or racemic (.+-.) form, is employed as the starting material, the process in one embodiment also being productive of the useful intermediate compound 4-methoxy-6,11-dihydroxy-7,8-dihydro-5,9(10H),12-naphthacenetrione. The process involves converting 7-deoxydaunomicinone successively to daunomycinone, adriamycinone, 14-0-p-anisyldiphenylmethyladriamycinone and finally to adriamycin or to both adriamycin and 7,9-epiadriamycin. When producing the latter mixture of diastereomers, the 7-deoxydaunomycinone starting material is first converted to racemate form by a process involving the successive production of 7-deoxydaunorubicinol, 4-methoxy-6,11-dihydroxy-7,8-dihydro-5,9(10H), 12-naphthacenetrione, (.+-.)-4-methoxy-9-cyano-6,9,11-trihydroxy-7,8,9,10-tetrahydro-5,12-naphth acenedione, (.+-.)-4-methoxy-9-cyano-9-(2'-tetrahydropyranyloxy)-6,11-dihydroxy-7,8,9, 10-tetrahydro-5,12-naphthacenedione and (.+-.)-7-deoxydaunomycinone.

REFERENCES:
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patent: 3862225 (1975-01-01), Conover et al.
Arcamone et al., Gazny Chimie Ital., vol. 100, 11, pp. 949-980 (1970).
Arcamone et al., J.A.C.S., vol. 86, pp. 5334-5335.

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