Abstract
First syntheses of C6,7 and C7 enantiopure cocaine analogues were achieved from d-(-)-ribose via a trans-acetonide controlled endo-selective intramolecular nitrone-alkene cycloaddition (INAC) as the key step. This synthetic scheme allows practical preparation of cocaine analogues for bioevaluation as potential candidates for the treatment of cocaine addiction and as potential conjugates for immunotherapy.
| Original language | English |
|---|---|
| Pages (from-to) | 2916-2919 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 13 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - 2011 Jun 3 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Shing, T. K. M., & So, K. H. (2011). Facile and enantiospecific syntheses of (6 S,7 R)-6-chloro-7-BENZYLOXY-, (7 S)-halo-, and (7 S)-hydroxy-cocaine and natural (-)-cocaine from d -(-)-ribose. Organic Letters, 13(11), 2916-2919. https://doi.org/10.1021/ol2009686