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 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Physical and Theoretical Chemistry
Cite this
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. / Shing, Tony Kung Ming; So, King H.
In: Organic Letters, Vol. 13, No. 11, 03.06.2011, p. 2916-2919.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - 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
AU - Shing, Tony Kung Ming
AU - So, King H.
PY - 2011/6/3
Y1 - 2011/6/3
N2 - 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.
AB - 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.
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UR - http://www.scopus.com/inward/citedby.url?scp=79957808833&partnerID=8YFLogxK
U2 - 10.1021/ol2009686
DO - 10.1021/ol2009686
M3 - Article
C2 - 21545090
AN - SCOPUS:79957808833
VL - 13
SP - 2916
EP - 2919
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 11
ER -