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The Faworskii rearrangement in the formation of 17-methyl steroids : The configuration of C-17 bromides
Affiliation:1. Research School of Chemistry, Australian National University, Canberra, ACT, 2601, Australia;2. Racing NSW−Australian Racing Forensic Laboratory, Sydney, NSW, 2000, Australia;1. State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, PR China;2. Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine University, 40225 Duesseldorf, Germany;1. Department of Pharmacology and Toxicology University of Arkansas for Medical Sciences, Little Rock, Arkansas 72205, USA;2. Research Triangle Institute, Research Triangle Park, NC 27709, USA
Abstract:The configuration of 17-bromo-20-keto pregnanes and the 17-methyletianic esters have been determined. The Faworskii rearrangement of the former to give the latter has been observed to be abnormal. It is suggested that C-17 → C-21 halogen transfer intervenes.
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