The Journal of Organic Chemistry

Short synthesis of (.+-.)-5-(3-furyl) octahydro-8-methylindolizines, alkaloids related to a component of Castoreum. Use of radical cyclization

DLJ Clive, RJ Bergstra

Index: Clive, Derrick L. J.; Bergstra, Raymond J. Journal of Organic Chemistry, 1991 , vol. 56, # 16 p. 4976 - 4977

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Citation Number: 33

Abstract

11 10 and these have the relative stereochemistries shown in 2,'3, 4 and 4.6 The latter was made from the bicyclic ketone 5 (obtained as a mixture of stereoisomers) by base-catalyzed equilibration and removal of the carbonyl (C 4-CH2). We report here an alternative and very short route to a ketone of gross structure 5 and its conversion into 2. Our bicyclic ketone 5 was identical ('H NMR) with the major isomer obtained previously, h and so the present ...