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 language | English (US) |
|---|---|
| Pages (from-to) | 4425-4428 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 40 |
| Issue number | 23 |
| DOIs | |
| State | Published - Jun 4 1999 |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Simoni, D., Roberti, M., Rondanin, R., & Kozikowski, A. P. (1999). Enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-oxa-norcocaines and 8-oxa-pseudonorcocaines. Tetrahedron Letters, 40(23), 4425-4428. https://doi.org/10.1016/S0040-4039(99)00763-7