Processes for producing doxorubicin, daunomycinone, and derivati

Details Processes for producing doxorubicin, daunomycinone, and derivati Processes for producing doxorubicin, daunomycinone, and derivati

1990-06-22

1993-04-06

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

552201, 552202, 549363, C07H 1524

Patent

active

052005135

ABSTRACT:
To produce doxorubicin and its analogues methyl 3alpha, 5alpha-dihydroxy-5beta-(trimethylsilylethynyl)-2alpha-nitromethylcyclohexa ne-1beta-carboxylate acetonide is condensed with 1,4-dihydro-4,4,5-trimethoxy-1-oxonaphthalene in the presence of 1,8-diazabicyclo-[5.4.0]undec-7-ene in an aprotic solvent to produce 3-[ (2beta-carbomethoxy-4beta-ethynyl-4alpha, 6alpha-(di-O-isopropylidenyl)cyclohexanyl-1-yl]-nitromethyl-4,4,5-trimetho xy-1-oxo-1,2,3,4-tetrahydronaphthalene; which is cyclized to produce 9beta-ethynyl-12-hydroxy-7alpha,9alpha-(di-O-isopropylidenyl)-6-nitro-4,5, 5-trimethoxy-5,5a,6,6a,7,8,9,10,10a,11-decahydro -11-naphthacenone. The decahydro-11-naphthacenone is converted to 7alpha-9alpha,(di-O-isopropyl-idenyl)-4,5-dimethoxy-9beta-ethynyl-12-hydro xy-6-nitro-6,6a,7,8,9,10,10a,11-octahydro-11, -naphthacenone. The octahydro-11-naphthacenone is oxidized to 7alpha-9alpha, (di-O-isopropyl-idenyl)-9beta-ethynyl-11-hydroxy-4-methoxy-6-nitro-7,8,9,1 0,-tetrahydro-5,12-naphthacenedione which is converted to 6-desoxy-6-nitrodaunomycinone, daunomycinone and related 6-substituted analogues of daunomycinone.

REFERENCES:
patent: 4697005 (1987-09-01), Swenton et al.
Swenton et al., II Jol. Amer. Chem. Soc., vol. 100(19), Sep. 1978, pp. 6188-6195, "A Regiospecific Synthesis of the Anthracyclic Aglycones, Daunomycinone and Adriamycinone".

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