Synthesis of dideoxyzearalane and related compounds

Claim 1

A method for preparing a deoxyzearalane type compound of the formula ##STR12## comprising reacting a hydroxy compound of the formula ##STR13## with an organic sulfonyl chloride of the formula RSO.sub.2 Cl under esterifying conditions which conditions include a non-reactive, aromatic or lower aliphatic organic reaction solvent containing an organic base selected from the group consisting of pyridine and tertiary lower aliphatic amines of from about 6 to 10 carbon atoms in an amount at least equimolar to the organic sulfonyl chloride; and a reaction temperature of from about 0° to about 75° C, to form a sulfonate ester derivative of the formula ##STR14## recovering the sulfonate ester derivative; and catalytically hydrogenolyzing the sulfonate ester derivative at a temperature of from about 100° to about 250° C at a hydrogen pressure of from about 200 to about 1000 pounds per square inch (about 14.1 to about 70.4 kilograms per square centimeter), in the presence of a catalyst selected from the group consisting of platinum, palladium, and Raney nickel, in a non-reactive, aromatic or lower aliphatic organic solvent containing a proton acceptor selected from the group consisting of pyridine, any isomeric form of lutidine, and tertiary lower aliphatic amines of from about 6 to 10 carbon atoms in an amount at least equivalent to the alkyl sulfonate ester groups, thereby forming the deoxyzearalane type compound; wherein D is selected from the group consisting of --CH 2 --, >C═O, and >CHOH; E is the same as D except when D is >CHOH, E is --CH 2 --; X may be a single bond or a double bond; G is the same as D, except when D is >CHOH, G is >CH--O--SO 2 R; and R is selected from the group consisting of lower alkyl of from 1 to about 5 carbon atoms.

Claim 2

A method for preparing a deoxyzearalane type compound of the formula ##STR12## comprising reacting a hydroxy compound of the formula ##STR13## with an organic sulfonyl chloride of the formula RSO.sub.2 Cl under esterifying conditions which conditions include a non-reactive, aromatic or lower aliphatic organic reaction solvent containing an organic base selected from the group consisting of pyridine and tertiary lower aliphatic amines of from about 6 to 10 carbon atoms in an amount at least equimolar to the organic sulfonyl chloride; and a reaction temperature of from about 0° to about 75° C, to form a sulfonate ester derivative of the formula ##STR14## recovering the sulfonate ester derivative; and catalytically hydrogenolyzing the sulfonate ester derivative at a temperature of from about 100° to about 250° C at a hydrogen pressure of from about 200 to about 1000 pounds per square inch (about 14.1 to about 70.4 kilograms per square centimeter), in the presence of a catalyst selected from the group consisting of platinum, palladium, and Raney nickel, in a non-reactive, aromatic or lower aliphatic organic solvent containing a proton acceptor selected from the group consisting of pyridine, any isomeric form of lutidine, and tertiary lower aliphatic amines of from about 6 to 10 carbon atoms in an amount at least equivalent to the alkyl sulfonate ester groups, thereby forming the deoxyzearalane type compound; wherein D is selected from the group consisting of --CH 2 --, >C═O, and >CHOH; E is the same as D except when D is >CHOH, E is --CH 2 --; X may be a single bond or a double bond; G is the same as D, except when D is >CHOH, G is >CH--O--SO 2 R; and R is selected from the group consisting of lower alkyl of from 1 to about 5 carbon atoms.