Zur Stereochemie der Vitamin D3-Epoxide Röntgenstrukturanalyse einer 5,6-7,8-Diepoxidverbindung |
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| Authors: | Wolfgang Reischl Harald Bernhard Christoph Kratky Erich Zbiral |
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| Institution: | (1) Institut für Organische Chemie, Universität Wien, A-1090 Wien, Österreich;(2) Institut für Physikalische Chemie, Universität Graz, A-8010 Graz, Österreich |
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| Abstract: | Epoxidation of vitamin D3 with benzonitrile ¦H2O2¦ KHCO3 (Payne's reagent) yields exclusively the 5,6-mono-oxirane2. Further epoxidation with the same reagent gives the 5,6-7,8-bisepoxide3 a. Its stereochemistry and therefore the stereochemistry of2 was established by single crystal X-ray analysis of thep-Brbenzoate3b. Thereby for the first time a directive effect of a homoallylic hydroxyl group during thePayne-epoxidation was established.Herrn Prof.Mihailovic (Universität Belgrad) mit den besten Wünschen zum 60. Geburtstag gewidmet. |
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| Keywords: | 5 6-Epoxy- and 5 6-7 8-bisepoxy vitamin D3 Stereochemistry |
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