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The synthesis of hydroxy-pyrrolizidines and indolizidines from cyclopropenones: towards hyacinthacines, australines and jenamidines

Hemming, Karl, Kondakal, Vishnu and Qamar, M. Ilyas (2012) The synthesis of hydroxy-pyrrolizidines and indolizidines from cyclopropenones: towards hyacinthacines, australines and jenamidines. Tetrahedron Letters, 53 (32). pp. 4100-4103. ISSN 0040-4039

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      Abstract

      The reaction of cyclic imines (1-pyrrolines and piperideines) with a cyclopropenone leads to pyrrolizidines and indolizidines, respectively, each with a hydroxy group on the carbon atom of the bridgehead. The cyclopropenone functions as an all-carbon 1,3-dipole equivalent towards the cyclic imine in this reaction, and the cyclic imines used include polyhydroxylated systems, thus allowing access to australine, alexine and hyacinthacine type compounds. The pyrrolizidine products contain the core of the jenamidine and bohemamine natural products which are of interest as cell-proliferation inhibitors and cell-cell adhesion inhibitors

      Item Type: Article
      Subjects: Q Science > QD Chemistry
      Schools: School of Applied Sciences
      Related URLs:
      Depositing User: Karl Hemming
      Date Deposited: 06 Dec 2012 15:42
      Last Modified: 30 May 2013 16:35
      URI: http://eprints.hud.ac.uk/id/eprint/16217

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