Synthesis of 2-alkoxyestradiols

Organic compounds -- part of the class 532-570 series – Organic compounds – Cyclopentanohydrophenanthrene ring system containing

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ABSTRACT:
Disclosed is a method of preparing a compound represented by the following structural formula: ##STR1## The method comprises reacting bromine (Br.sub.2) and an aliphatic organic acid with a compound represented by the following structural formula: ##STR2## R.sub.1 and R.sub.2 are each independently a hydroxyl protecting group.

REFERENCES:
patent: 5405944 (1995-04-01), Suzuki et al.
Slaunwhite et al., "Bromination of phenolic steroid. I. Substitution of estrone and 17beta-estradiol in ring A". J. Org. Chem. vol. 27, pp. 1749-1752, 1962.
He et al., "A versatile synthesis of 2-methoxyestradiol, an endogenous metabolite of estradiol which inhibits tubulin polymerization by binding to the colchicine binding site", Biorganic & Medicinal Chem. Lett. vol. 4(14), pp. 1725-1728, 1994.
Chen et al., "A New synthetic route 2-and 4-methoxyestradiols by nucleophilic substitution". Steroids, vol. 47(1), pp. 63-66, 1986.
Pert et al., "An alternative route to 2-bromo and 2-iodo-estradiols from estradiol". Aust. J. Chem., vol. 40, pp. 303-309, 1987.
Rao et al., "A novel, two-step synthesis of 2-methoxyestradiol". Synthesis, pp. 168-169, 1977.
D. J. Pert and D. D. Ridley, "Formylation of Oestrogens," Aust. J. Chem., 42:405-19 (1989).
S. Chen, et al., "A New Synthetic Route to 2-and 4-Methoxyestradiols by Nucleophilic Substitution," Steroids 47 (1) :63-66 (Jan. 1986).
P. N. Rao and J. E. Burdett, Jr., "Novel Two-Step Synthesis of 2-Methoxyestradiol," Synthesis, pp. 168-169 (Mar. 1977).
H. M. He, et al., "A Novel 1,3 O.fwdarw.C Silyl and Deacylation Reaction Mediated by Tetra-n-butylammonium Fluoride in an Aromatic System," J. Org. Chem., 60:5905-5909 (1995).
W. R. Slaunwhite, Jr., and L. Neeley, Bromination of Phenolic Steroids. I. Substitution of Estrone and 17.beta.-Estradiol in Ring A.sup.1 Bromination of Phenolic Steroids I, J. Org. Chem. 27:1749-1752 (1962).
M. Cushman, et al., "Synthesis, Antitubulin and Antimitotic Activity, and Cytotoxicity of Analogs of 2-Methoxyestradiol, an Endogenous Mammalian Metabolite of Estradiol that Inhibits Tubulin Polymerization by Binding to the Colchicine Binding Site," J. Med. Chem. 38:2041-2049 (1995).
H. M. He and M. Cushman, "A Versatile Synthesis of 2-Methoxyestradiol, An Endogenous Metabolite of Estradiol which Inhibits Tubulin Polymerization by Binding to the Colchicine Binding Site," Biorganic & Medicinal Chemistry Letters, 4(14) :1725-1728 (1994).
Cushman, M., et al., "Synthesis of Analogs of 2-Methoxyestradiol with Enhanced Inhibitory Effects on Tubulin Polymerization and Cancer Cell Growth," J. Med. Chem. 40:2323-2334 (1997).
Numazawa, M. et al., "Synthesis of 2-Methoxy-and 4-Methoxy-Estrogens with Halogen-Methoxy Exchange Reaction," J. Chem. Res. Miniprint 11:3701-3715, Paper E/155/85 (Dec. 31, 1984).
Nambara, T., et al. "Studies on Steroid Conjugates. III. New Synthesis of 2-Methoxyestrogens," Chem. Pharm. Bull. 18 (3) :474-480 (1970).
Zheng, X-h, et al., "A New Synthetic Route to Pyrogallolestrogen Dimethyl Ethers by Nucleophilic Substitution of 2,4-Dibromoestrogens," Steroids 40 (2) :121-124 (1982).
Horiuchi, C.A., et al., "Novel Regioselective Iodination of Estradiol 17.beta.-Acetate," Bull. Chem. Soc. Jpn. 59(8) :2459-2462 (1986).

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