Enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-oxa-norcocaines and 8-oxa-pseudonorcocaines

Daniele Simoni, Marinella Roberti, Riccardo Rondanin, Alan P. Kozikowski

Research output: Contribution to journalArticle

Abstract

The enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3- one with chiral lithium amides 5 and 6, in the presence of LiCl, gave the chiral lithium enolates which were in turn reacted with methyl cyanoformate. The resulting chiral β-keto esters were reduced with sodium amalgam to afford the 8-oxa-ecgonine- and 8-oxa-pseudoecgonine-like derivatives which allowed facile preparation of the (+)- and (-)-8-oxa-norcocaines and (+)- and (-)-8-oxa-pseudonorcocaines. The new synthesized 8-oxa analogues of cocaine showed good enantiomeric excesses in the range of 84-90%.

Original languageEnglish (US)
Pages (from-to)4425-4428
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number23
DOIs
StatePublished - Jun 4 1999

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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