Title:
PRODUCTION OF (+)-ESTRONE DERIVATIVE
Document Type and Number:
Japanese Patent JP3178046
Kind Code:
B2
Abstract:
PURPOSE: To obtain the subject derivative in good yield in a few steps by using a specific compound as a starting substance and subjecting the compound and a 4-vinyl-7-alkoxy-1,2-dihydronaphthalene to the asymmetric Diels-Alder reaction.
CONSTITUTION: (-)-Tricyclo[5.2.1.02,6]deca-4,8-dien-3-one, expressed by formula I and used as a starting substance and a 4-vinyl-7-alkoxy-1,2-dihydronaphthalene expressed by formula II (R is 1-20C alkyl) are subjected to the asymmetric Diels-Alder reaction in the presence of a Lewis acid, preferably at -30°C to afford a compound expressed by formula III, which is then methylated with methyl iodide in the presence of a base to provide a compound expressed by formula IV. The resultant compound expressed by formula IV is subsequently treated with trifluoroacetic acid and triethylsilane to afford a compound expressed by formula V, which is then heated to provide a compound expressed by formula VI. The unsaturated bond is reduced by catalytic hydrogenation to afford the objective compound expressed by formula VII, e.g. estrone methyl ether.
Inventors:
Seiichi Takano
Kuniro Ogasawara
Kuniro Ogasawara
Application Number:
JP33455491A
Publication Date:
June 18, 2001
Filing Date:
November 25, 1991
Export Citation:
Assignee:
Chisso Corporation
International Classes:
C07J1/00; C07J53/00; C07J75/00; (IPC1-7): C07J1/00
Attorney, Agent or Firm:
Eiko Funahashi