The Journal of organic chemistry

Synthesis of pipecolic acid-based spiro bicyclic lactam scaffolds as β-turn mimics

RV Somu, RL Johnson

Index: Somu, Ravindranadh V.; Johnson, Rodney L. Journal of Organic Chemistry, 2005 , vol. 70, # 15 p. 5954 - 5963

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Citation Number: 22

Abstract

A series of 6.5. 5 spiro bicyclic lactam scaffolds were synthesized from pipecolic acid in a sequence of reactions that was initiated with the α-allylation of tert-butoxycarbonyl pipecolic acid. Oxidative cleavage of the olefin to give an aldehyde followed by condensation with d- cysteine methyl ester gave a mixture of pipecolyl thiazolidines. Cyclization of the pipecolyl thiazolidines with Mukaiyama's reagent yielded the spiro bicyclic lactams 4a-d. ...