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 language | English |
|---|---|
| Pages (from-to) | 5211-5213 |
| Number of pages | 3 |
| Journal | Tetrahedron Letters |
| Volume | 54 |
| Issue number | 38 |
| DOIs | |
| State | Published - 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.
Funding
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.
| Funders | Funder number |
|---|---|
| National Institutes of Health (NIH) | U01 DA13519 |
Keywords
- Lobelane
- Norlobelane analogues
- Quinlobelane
- Swern oxidation
- Wittig reaction
- cis-2,6-Di-(2-quinolylpiperidine)
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry