Preparation of 3,17‐ and 3,20‐Difluoro‐Derivatives of the Androst‐5‐ene and Pregn‐5‐ene Series

Abstract

Unsaturated mono‐ and difluorosteroids have been prepared in high yield using n‐perfluorobutanesulfonyl fluoride 1. The 3,17‐ and 3,20‐difluoro‐5,6‐dehydrosteroids are reported for the first time. 3‐Fluoroderivatives of the androst‐5‐ene‐17‐one and 5α‐androst‐17‐one series have been prepared, and yields obtained with 1 have been compared with those reported with other fluorinating agents.

Keywords:

• 3,17 and 3,20‐difluorosteroids; Fluorodehtdroxylation; n‐Perfluorosulfonyl fluoride

Acknowledgment

We acknowledge generous support from Quest International. We are grateful to Mike Cocksedge of the ULIRS for obtaining mass spectra.