Tetrahedron

Asymmetric synthesis of piperidines and octahydroindolizines using a one-pot ring-closure/N-debenzylation procedure

SG Davies, AM Fletcher, DG Hughes, JA Lee, PD Price…

Index: Davies, Stephen G.; Fletcher, Ai M.; Hughes, Deri G.; Lee, James A.; Price, Paul D.; Roberts, Paul M.; Russell, Angela J.; Smith, Andrew D.; Thomson, James E.; Williams, Oliver M.H. Tetrahedron, 2011 ,  vol. 67,  # 51  p. 9975 - 9992

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Citation Number: 31

Abstract

The conjugate addition of an enantiopure lithium amide to a ζ-hydroxy-α, β-unsaturated ester followed by a one-pot ring-closure/N-debenzylation protocol has been used in the asymmetric syntheses of (S)-coniine and (R)-δ-coniceine (isolated as the corresponding hydrochloride salts), and (R, R)-1-(hydroxymethyl) octahydroindolizine (the bicyclic fragment of stellettamides A–C).