Synthesis of the 6- and 7-hydroxylated cocaines and pseudococaines

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5333-5336

  Kozikowski, A P ^a   Simoni, D ^c   Manfredini, S ^c   Roberti, M ^c   Stoelwinder, J ^b  

^a GEORGETOWN UNIVERSITY MEDICAL CENTER   (United States)

^b MAYO CLINIC   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

COCAINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030598004     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01123-9     Document Type: Article

References (10)

1. 1. Lounasmaa, M. The Alkaloids 1988, 33, 1.
2. 2. (a) Woolverton, W. L.; Johnson, K. M. Trends Pharmacol. Sci. 1992, 13, 193;
3. (b) Woolverton, W. L.; Kleven, M. S. NIDA Research Monograph 1988, 88, 160.
4. 3. Simoni, D.; Stoelwinder, J.; Kozikowski, A. P.; Johnson, K. M.; Bergmann, J. S.; Ball, R. G. J. Med. Chem. 1993, 36, 3975.
5. 4. Kozikowski, A. P.; Eddine Saiah, M. K.; Johnson, K. M.; Bergmann, J. S. J. Med. Chem. 1995, 38, 3086 and references cited therein.
6. 5. Kozikowski, A. P.; Simoni, D.; Baraldi, P. G.; Lampronti, I.; Manfredini, S. Bioorg. Med. Chem. Lett. 1996, 6, 441.
7. 6. Sheehan, J. C.; Bloom, B. M. J. Am. Chem. Soc. 1952, 74, 3825.
8. 7. Carroll, F. I.; Coleman, M. L.; Lewin, A. H. J. Org. Chem. 1982, 47, 13.
9. 3) δ 28.58, 34.60, 41.15, 42.90, 52.27, 58.34, 67.97, 69.88, 72.27, 128.40, 129.67, 130.19, 133.07, 165.54, 172.35.
10. 9. As another approach to the 6- and 7-functionalized analogues of cocaine and its Win derivatives, we note here that we have explored the "Katritzky-type" dipolar cycloaddition chemistry of 1-benzyl-3-oxidopyridinium with α-chloroacrylonitrile as dipolarophile to provide I, which has been further converted by standard chemistry to II. Additional details of this work will be reported separately. (equation presented)