Imc Chemical Group, Inc.

Commercial Solvents Corporation

Donald E Robertson

Frank Kavka

Wilbert Herbert Urry

A method is disclosed for preparing dideoxyzearalane and related compounds which comprises reacting an appropriate hydroxy compound with an organic sulfonyl chloride to form a sulfonate ester derivative; recovering the sulfonate ester derivative; and catalytically hydrogenolyzing the sulfonate ester derivative to form the desired product.

Synthesis of dideoxyzearalane and related compounds

A method is disclosed for preparing dideoxyzearalane and related compounds which comprises reacting a hexahydrozearalin with an organic sulfonyl chloride to form a sulfonate ester derivative; recovering the sulfonate ester derivative; and catalytically dehydrosulfonyloxylating and aromatizing the sulfonate ester derivative to form the desired product.

Compounds of the formula: ##SPC1## Wherein --A-- is either --CH.sub.2 --CH.sub.2 -- or --CH=CH--, &gt;Z is either &gt;CH.sub.2, &gt;C=O or &gt;CH--OH, Y is --H or --OR' wherein R' can be hydrogen, alkyl, alkanoyl, aryl, or aryl alkyl, and Gly is a glycosyl group, which exhibit anabolic and estrogenic activity, are provided, as well as processes for their preparation and compositions containing them which are useful as ruminant growth promoters.

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Terre Haute, IN, United States of America

Donald E Robertson