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A New Chiral Director for the Highly Diastereoselective Borane Reductionof Steroid-20-ones
Authors:Gy?rgy G?nd?s  Gy?rgy Dombi and James C Orr
Institution:(1) Department of Biology, Lund University, S?lvegatan 37, 223 62 Lund, Sweden;(2) Department of Chemistry, Washington State University, Pullman, WA 99164-4630, USA;(3) School of Natural Sciences, Linneus University, 391 82 Kalmar, Sweden;(4) Department of Chemistry, Royal Institute of Technology, 100 44 Stockholm, Sweden;(5) Department of Chemical Ecology, G?teborg University, 400 33 G?teborg, Sweden;(6) Present address: Chemical Ecology, Department of Plant Protection Biology, Swedish University of Agricultural Sciences, P.O. Box 102, 230 53 Alnarp, Sweden
Abstract: The synthesis of a new chiral boroxazolidine was achieved which was used to control the stereochemistry of the borane reduction of the 20-keto group of steroids. The otherwise hardly accessible 20α-(20S)-alcohol can thus be prepared in a yield of 91%.
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