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. 4100-4130. ISSN 0040-4039

PDF (accepted unpaginated copy) - Accepted Version Download (648kB)

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
Contributors:	Contribution Name Email ORCID Author Hemming, Karl k.hemming@hud.ac.uk UNSPECIFIED Author Kondakal, Vishnu UNSPECIFIED UNSPECIFIED Author Qamar, M. Ilyas UNSPECIFIED UNSPECIFIED
Subjects:	Q Science > QD Chemistry
Schools:	School of Applied Sciences
Related URLs:	Author
Depositing User:	Karl Hemming
Date Deposited:	08 Aug 2012 14:05
Last Modified:	28 Aug 2021 20:38
URI:	http://eprints.hud.ac.uk/id/eprint/14148

Available Versions of this Item

• The synthesis of hydroxy-pyrrolizidines and indolizidines from cyclopropenones: towards hyacinthacines, australines and jenamidines. (deposited 08 Aug 2012 14:05) [Currently Displayed]
  • The synthesis of hydroxy-pyrrolizidines and indolizidines from cyclopropenones: towards hyacinthacines, australines and jenamidines. (deposited 06 Dec 2012 15:42)

Downloads

Repository Staff Only: item control page

View Item