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Helvetica Chimica ActaVolume 74, Issue 7, 30 October 1991, Pages 1459-1463

Synthesis, structure, and reactivity of secosteroids containing a medium‐sized ring. Part 32. Conformations and photochemical reactivity of some unsaturated 5,10‐secosteroidal ketones(Article)

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  • aFaculty of Chemistry, University of Belgrade, P.O. Box 550, Belgrade, YU-11001
  • bResearch Laboratories, Pharmaceuticals Division, Ciba-Geigy Ltd., Basel, CH-4002, Switzerland
  • cCiba-Geigy Ltd., Basel, CH-4002, Switzerland
  • dInstitute of Chemistry, Technology and Metallurgy, Belgrade, YU-11001

Abstract

UV irradiation of the unsaturated (E)‐5,10‐secosteroidal ketones 1 and 6 results, in addition to (E/Z)‐isomeri‐zation, in an intramolecular Pateino‐Büchi reaction and, in the case of 1, in transannular cyclization (along with AcOH elimination). The stereochemistry of the observed intramolecular photoprocesses can be explained in terms of ground‐state conformations of the (E)‐seco‐ketones 1 and 6 in solution. Copyright © 1991 Verlag GmbH & Co. KGaA, Weinheim

  • ISSN: 0018019X
  • Source Type: Journal
  • Original language: English
  • DOI: 10.1002/hlca.19910740709
  • Document Type: Article

  Mihailović, M.Lj.; Faculty of Chemistry, University of Belgrade, P.O. Box 550, Belgrade,
© Copyright 2016 Elsevier B.V., All rights reserved.

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