Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition

Stephen G. Davies, Ai M. Fletcher, Paul M. Roberts, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

81 Citations (Scopus)

Abstract

Conjugate addition of lithium (R)-N-allyl-N-(alpha-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(alpha-methylbenzyl)amide to an alkyl hexa-2,4-dienoate or alkyl hepta-2,6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant P-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed to a range of piperidine alkaloids of the Sedum family, and the corresponding five-, seven- and eight-membered ring homologues. (C) 2009 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)10192-10213
Number of pages22
JournalTetrahedron
Volume65
Issue number49
DOIs
Publication statusPublished - 5 Dec 2009

Keywords

  • Lithium amides
  • Asymmetric synthesis
  • Ring-closing metathesis
  • Sedum alkaloids
  • Sedamine
  • CORRESPONDING BETA,GAMMA-UNSATURATED ESTERS
  • SHORT ENANTIOSELECTIVE SYNTHESIS
  • RING CLOSING METATHESIS
  • STEREOSELECTIVE-SYNTHESIS
  • PIPERIDINE ALKALOIDS
  • (E)-ALPHA,BETA-UNSATURATED ESTERS
  • SUBSTITUTED PIPERIDINES
  • ABSOLUTE-CONFIGURATION
  • (S)-HOMOPIPECOLIC ACID
  • LOBELIA-INFLATA

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