Processes for producing doxorubicin, daunomycinone, and derivati

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

1992-07-16

1997-01-14

Ivy, C. Warren

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

Organic compounds

Tetracyclo naphthacene configured ring system having at...

552206, C07H 1524

Patent

active

055941583

ABSTRACT:
Daunomycinone is a known precursor of the well known antibiotic and antineoplastic, doxorubicin. Daunomycinone may be synthesized by preparing mono ketal of a 1,4-naphthoquinone as the precursor of the CD rings of daunomycinone followed by preparing a precursor for ring A with C.sub.6 and C.sub.11 attached and the stereochemistry at C.sub.7 and C.sub.9 established and coupling it to CD and then completing ring B.

REFERENCES:
patent: 4515720 (1985-05-01), Hauser et al.
patent: 5001243 (1991-03-01), Fischer et al.
Studies in the Synthesis of Adriamycin, D. Wheeler, et al., "New Trends In Natural Products Chemistry", 1986, pp. 565-583.
A Short and Efficient Synthesis of 11-Deoxyanthracyclinones: Strong Base-Induced Cycloaddition of the Suitably Substituted Tetrahydrohomophthalic Anhydride, Y. Tamura, et al., "Tetrahedron Letters", vol 26, No. 12, pp. 1549-1552, 1985.
Conjugate Addition of Acylate-Nickel Complexes to Quinone Monoketals: Formal Synthesis of the Naphthoquinone Antibiotics Nanaomycin A and Deoxyfrenolicin, M. F. Semmelhack, et al., "J. Org. Chem.", vol. 50, 1985, pp. 5566-5574.

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