The Journal of Organic Chemistry

Thiol esters from steroid 17. beta.-carboxylic acids: carboxylate activation and internal participation by 17. alpha.-acylates

DJ Kertesz, M Marx

Index: Kertesz, Denis J.; Marx, Michael Journal of Organic Chemistry, 1986 , vol. 51, # 12 p. 2315 - 2328

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Citation Number: 57

Abstract

The chemistry of the steroid 17@-carboxylic acids derived from 16, 17a-disubstituted corticosteroids was investigated with respect to thiol ester formation. Major quantities of 17- spiro byproducts were observed in the reactions of 16-methyl-17a-acyloxy acids, and the degree of 17-ester participation leading to these structures was dependent on the carboxylate activating group used and stereochemistry at C-16. Diethyl phosphate mixed ...