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
Externally publishedYes

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Deprotonation
Lithium
Mercury amalgams
Cocaine
Amides
Esters
Sodium
Derivatives
ecgonine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3-one : Synthesis of 8-oxa-norcocaines and 8-oxa-pseudonorcocaines. / Simoni, Daniele; Roberti, Marinella; Rondanin, Riccardo; Kozikowski, Alan P.

In: Tetrahedron Letters, Vol. 40, No. 23, 04.06.1999, p. 4425-4428.

Research output: Contribution to journalArticle

Simoni, Daniele ; Roberti, Marinella ; Rondanin, Riccardo ; Kozikowski, Alan P. / Enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3-one : Synthesis of 8-oxa-norcocaines and 8-oxa-pseudonorcocaines. In: Tetrahedron Letters. 1999 ; Vol. 40, No. 23. pp. 4425-4428.
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