Efficient synthesis of cis-2,6-di-(2-quinolylpiperidine)

Derong Ding, Linda P. Dwoskin, Peter A. Crooks

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

An efficient synthesis of cis-2,6-di-(2-quinolylpiperidine) has been developed. The key steps involve Wittig reaction of N-Cbz-protected cis-piperidine-2,6-dicarboxaldehyde (3) with 2-(triphenylphosphinyl-methyl) quinoline bromide (4) and sequential removal of the N-Cbz group and double bond reduction. This synthetic procedure provides an efficient preparation for this useful norlobelane analogue.

Original languageEnglish
Pages (from-to)5211-5213
Number of pages3
JournalTetrahedron Letters
Volume54
Issue number38
DOIs
StatePublished - Sep 18 2013

Bibliographical note

Funding Information:
The authors gratefully acknowledge support from NIH grant U01 DA13519 . The University of Kentucky holds patents on lobeline and the analogues described in the current work. A potential royalty stream to LPD and PAC may occur consistent with University of Kentucky policy.

Keywords

  • Lobelane
  • Norlobelane analogues
  • Quinlobelane
  • Swern oxidation
  • Wittig reaction
  • cis-2,6-Di-(2-quinolylpiperidine)

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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