Method of synthesizing a late-stage intermediate to 11-deoxydaun

Details Method of synthesizing a late-stage intermediate to 11-deoxydaun Method of synthesizing a late-stage intermediate to 11-deoxydaun

1983-03-11

1985-05-07

Hollrah, Glennon H.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603515, 260365, 260376, C07C 5022, C07C 5036

Patent

active

045157200

ABSTRACT:
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.

REFERENCES:
patent: 4215062 (1980-07-01), Mitscher
patent: 4244880 (1981-01-01), Alexander et al.
patent: 4264510 (1981-04-01), Vogel et al.

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