Method for producing (+)-estrone derivatives

Details Method for producing (+)-estrone derivatives Method for producing (+)-estrone derivatives

1994-07-18

1995-06-13

Mars, Howard T.

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

Organic compounds

Cyclopentanohydrophenanthrene ring system containing

C07J 100

Patent

active

054244625

ABSTRACT:
The present invention provides a method for producing (+)-estrone derivatives, characterized in that it comprises starting from a certain cyclopentadiene derivative, reacting the derivative with a certain diene compound by an asymmetric Diels-Alder reaction, and via intermediates obtaining a (+)-estron derivative represented by the following formula: ##STR1## wherein R is alkyl of 1-20 carbon atoms. According to the present invention, (+)-estron derivatives can be obtained by limited steps from the starting materials of dicyclopentadiene derivatives.

REFERENCES:
patent: 3451892 (1969-06-01), Herzog et al.
CA 85(7): 46943t 1976.
Takano et al, Concise Enantio-and Stereo-controlled Synthesis of (+)-Equilenin using Chiral Cyclopentadienone Synthon, Journal of the Chemical Society, Chemical Communications, No. 21, pp. 1544-1546, Nov. 1, 1990.
Quinkert et al, E. Dane's Route to Estrone Revisited, Tetrahedron Letters, vol. 32, No. 28, pp. 3357-3360, 1991.
Douglas F. Taber et al, "Enantioselective Ring Contruction: Synthesis of (+)-Estrone Methyl Ether," J. Organ. Chem., pp. 28-34 (1987).
Gary Posner et al, "Total Synthesis of Natural Estrone and Estradiol Methyl Ethers in Extremely High Enantiomeric Purity via an Asymmetric Michael Addition to an Unsaturated Sulfoxide," J. Am. Chem. Soc., pp. 1239-1244 (1986).
G. S. R. Subba Rao et al, "Synthesis Based on Cyclohexadienes. V* A New Approach to the Synthesis of hd a-Ring Aromatic Steroids: A Formal Total Synthesis of (+)-Esterone," Aust. J. Chem., pp. 187-203 (1992).
Seiichi Takano et al, "A Concise Stereocontrolled Total Synthesis of (+)-Esterone," Tetrahedron Letters, vol. 33, No. 14, pp. 1909-1910 (1992).

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