Synthesis of (+)-4-demethoxydaunomycinone

Details Synthesis of (+)-4-demethoxydaunomycinone Synthesis of (+)-4-demethoxydaunomycinone

1983-05-13

1984-12-18

Hollrah, Glennon H.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

2603511, 2603515, 260365, 260376, C07C 5036, C07D30337

Patent

active

044892063

ABSTRACT:
It has been found that stereospecific R(-)-4-demethoxy-7-deoxydaunomycinone can be synthesized from the known compound 4-demethoxy-7,9-dideoxydaunomycinone. R(-)-4-Demethoxy-7-deoxy-daunomycinone is an intermediate in the synthesis of (+)-4-demethoxydaunomycinone, the aglycone of the nonnaturally occurring and antitumor active (-)7(S)9(S)-4-demethoxydaunorubicin.

REFERENCES:
patent: 4229355 (1980-10-01), Penco et al.
patent: 4298535 (1981-11-01), Vogel et al.
Tetrahedron Letters, No. 27, pp. 2303-2306, "Synthesis of Anthracyclinones via Base-Catalyzed Cyclizations of Dihydroanthraquinone Dev.", Suzuki et al., 1977.
Tetrahedron Letters, vol. 21, pp. 2753-2756, "Asymmetric Synthesis of Optically Pure (R)(-)-2-acetyl-5,8-Dimethoxy-1,2,3,4-tetrahydro-2-napthol", Terashima, 1980.
Canadian Journal of Chemistry, vol. 49, pp. 2712-2718, "Synthetic Studies of Hydronapthaceric Antibiotics", Wong et al., 1971.
JACS, vol. 100, No. 11, pp. 3635-3636, "A Novel Synthesis of (.+-.)-4-Demethoxydaunomycinone" Kerdesky et al., 1978.
Canadian Journal of Chemistry, vol. 51, pp. 466-467, "The Total Synthesis of Daunomycinone" Wong et al., 1972.
J. Chem. Soc. Chem. Commun., 1982, pp. 158-160, Broadharet et al.
J. C. S. Chem. Commun., 1981, pp. 1100-1101, "Preparation of (-)-(7R) Acetyl-7-Hydroxy-4,4-dimethoxy-5,6,7,8-tetrahydronaphthalen-1 (4H)-one", Warrener, 1981.

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