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Preparation of 3 alpha-Fluoro- and 3 beta-Fluoro derivatives of 5 alpha-androst-16-enes and androsta-5,16-dienes

Marson, CM; Decreau, RA; Smith, KE; (2002) Preparation of 3 alpha-Fluoro- and 3 beta-Fluoro derivatives of 5 alpha-androst-16-enes and androsta-5,16-dienes. SYNTHETIC COMMUN , 32 (14) 2125 - 2135. 10.1081/SCC-120005419.

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Abstract

n-Perfluorobutanesulfonyl fluoride, in the presence of DBU, is shown to be a convenient and satisfactory reagent for the preparation of a variety of unsaturated 3-fluorosteroids of defined stereochemistry. 3-Fluoro-16,17-dehydrosteroids are reported for the first time. Fluorodehydroxylation proceeded with retention of configuration for 5,6,16,17-tetradehydro-3beta-sterols, but with inversion for their 3alpha-analogues, as it did for several 16,17-dehydrosterols.

Type:Article
Title:Preparation of 3 alpha-Fluoro- and 3 beta-Fluoro derivatives of 5 alpha-androst-16-enes and androsta-5,16-dienes
DOI:10.1081/SCC-120005419
Keywords:3-Fluorosteroids, fluorodehydroxylation, n-perfluorobutanesulfonyl fluoride, STEROIDS, MECHANISM, ALCOHOLS, SWEAT
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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