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Tetrahedron LettersVolume 32, Issue 51, 16 December 1991, Pages 7605-7608

Oxidative hydrolysis and acid-catalyzed rearrangement of steroidal isoxazolidines(Article)

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  • Faculty of Chemistry, University of Belgrade, Studentski trg 16, P.O. Box 550, YU-11001 Belgrade, Yugoslavia, and Institute of Chemistry, Technology and Metallurgy, Belgrade, Yugoslavia

Abstract

Treatment of steroidal isoxazolidines 3a, 3b and 5b with N-methylhydroxylamine hydrochloride in boiling ethanol-pyridine (1:1) solution results in elimination of the CH3NH2fragment, affording products of oxidative hydrolysis 4a, 4b, and 6b, while acid-catalyzed reaction of isoxazolidines 2a, 3a and 5b leads to rearrangement involving the N-CH3 group with formation of the perhydro-3,1-oxazine derivatives 8a, 9a and 10b. © 1991.

Author keywords

1-oxazinesacid-catalyzed rearrangementoxidative hydrolysisstereoidal perhydro-3steroidal isoxazolidines

Indexed keywords

EMTREE drug terms:isoxazolidine derivativesteroid
EMTREE medical terms:articlepriority journalreaction analysissynthesis
Species Index:Staphylococcus phage 3A

Funding details

  • 1

    AcknowledgementT: he authorsa re gratefult o the SerbianA cademyo f Sciencesa nd Arts and to the SerbianR epublicR esearchF und for financial support.

  • ISSN: 00404039
  • CODEN: TELEA
  • Source Type: Journal
  • Original language: English
  • DOI: 10.1016/0040-4039(91)80546-I
  • Document Type: Article

  Rajković, M.;
© Copyright 2014 Elsevier B.V., All rights reserved.

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