Oregon Graduate Center for Study and Research

Frank M Hauser

Dipakranjan Mal

The compound 6-acetyl-4a,5,6,7,8,8a-hexahydro-1(4H)-naphthalenone, and preparation thereof beginning from 2-(2-hydroxyethyl)bicyclo[2.2.2] oct-5-ene.

Production of a hexahydronaphthalenone compound

Preparation of 9-acetyl-6-hydroxy-4-methoxy-7,8,9,10-tetrahydronaphthacene-5,12-dione (the object intermediate), and precursor compounds to the object intermediate. Preparation of the object intermediate according to the invention begins from 2-(2-hydroxyethyl)-bicyclo[2.2.2]oct-5-ene, wherein the latter is converted to 6-acetyl-4a,5,6,7,8,8a-hexahydro-1(4H) naphthalenone (one of the two precursor compounds) which is subsequently reacted with a phenylsulfonyl isobenzofuranone to furnish, regiospecifically, 9-acetyl-5,12-dihydroxy-4-methoxy-6(11H)-hexahydronaphthacenone (the other of the two precursor compounds). Heating the hexahydronaphthacenone in dimethylforamide under an oxygen atmosphere gives the object intermediate.

Growing community of inventors

Portland, OR, United States of America

Frank M Hauser