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

VVR Kondakal, MI Qamar, K Hemming

Index: Kondakal, Vishnu V.R.; Ilyas Qamar; Hemming, Karl Tetrahedron Letters, 2012 , vol. 53, # 32 p. 4100 - 4103

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Citation Number: 9

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 at 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. ...