Asymmetric Synthesis of Piperidines and Octahydroindolizines

Stephen G. Davies, Deri G. Hughes, Paul D. Price, Paul M. Roberts, Angela J. Russell, Andrew D. Smith, James E. Thomson, Oliver M. H. Williams

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

Abstract

The conjugate addition of a homochiral lithium amide to a xi-hydroxy-alpha,beta-unsaturated ester, followed by a one-pot, ring-closure-N-debenzylation protocol has been used in the asymmetric syntheses of (S)-coniine and (R)-delta-coniceine (isolated as the corresponding hydrochloride salts) and the bicyclic core of stellettamide A.

Original languageEnglish
Pages (from-to)567-570
Number of pages4
JournalSynlett
Issue number4
DOIs
Publication statusPublished - Mar 2010

Keywords

  • asymmetric synthesis
  • lithium amides
  • piperidines
  • coniine
  • delta-coniceine
  • JASPINE-B PACHASTRISSAMINE
  • AMIDE CONJUGATE ADDITION
  • D-LYXO-PHYTOSPHINGOSINE
  • BETA-AMINO ACIDS
  • ENANTIOSELECTIVE SYNTHESIS
  • PUMILIOTOXIN ALKALOIDS
  • DERIVATIVES
  • INDOLIZIDINE
  • ALKYLATION
  • EFFICIENT

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