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

Journal article

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). © 2011 Elsevier Ltd. All rights reserved.

Authors: Davies, S; Fletcher, A; Hughes, D; Lee, J; Price, P

• Publication status: Published
• Journal: TETRAHEDRON
• Volume: 67
• Issue: 51
• Pages: 9975-9992
• Publication date: 2011-12-23
• DOI: 10.1016/j.tet.2011.09.038
• EISSN: 1464-5416
• ISSN: 0040-4020
• Language: English
• Keywords: Asymmetric synthesis; Piperidines; delta-Coniceine; Lithium amide; Coniine