Synthesis of 5-endo-, 5-exo-, 6-endo- and 6-exo-hydroxylated analogues of epibatidine

Zhi Liang Wei, Clifford George, Alan P. Kozikowski

Research output: Contribution to journalArticle

Abstract

A convenient, high-yield synthesis of N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one (7) was developed by SmI2-mediated desulfonylation of 6. Thus, 5-endo-, 5-exo-, 6-endo-, and 6-exo-hydroxylated epibatidine analogues 2a,b and 3a,b were synthesized from 7 by using a Pd(PPh3)4-catalyzed reductive Heck coupling reaction and SmI2-mediated reduction of the carbonyl group as the key steps. Other reaction conditions for the reductive Heck procedure and the reduction step were also investigated.

Original languageEnglish (US)
Pages (from-to)3847-3850
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number19
DOIs
StatePublished - May 5 2003
Externally publishedYes

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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Synthesis of 5-endo-, 5-exo-, 6-endo- and 6-exo-hydroxylated analogues of epibatidine. / Wei, Zhi Liang; George, Clifford; Kozikowski, Alan P.

In: Tetrahedron Letters, Vol. 44, No. 19, 05.05.2003, p. 3847-3850.

Research output: Contribution to journalArticle

Wei, Zhi Liang ; George, Clifford ; Kozikowski, Alan P. / Synthesis of 5-endo-, 5-exo-, 6-endo- and 6-exo-hydroxylated analogues of epibatidine. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 19. pp. 3847-3850.
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