Enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-oxa-norcocaines and 8-oxa-pseudonorcocaines

Tetrahedron Letters

Volumn 40, Issue 23, 1999, Pages 4425-4428

  Simoni, Daniele ^a   Roberti, Marinella ^b   Rondanin, Riccardo ^a   Kozikowski, Alan P ^c  

^a Dipartimento di Scienze Farmaceutiche   (Italy)

^b Dipto di Scienze Farmaceutiche   (Italy)

^c GEORGETOWN UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 OXANORCOCAINE; 8 OXAPSEUDONORCOCAINE; LITHIUM CHLORIDE; NORCOCAINE; UNCLASSIFIED DRUG;

ARTICLE; BINDING KINETICS; CHIRALITY; COCAINE DEPENDENCE; DRUG BINDING; ENANTIOMER; HYDROXYLATION; PROTON TRANSPORT; STRUCTURE ANALYSIS;

EID: 0033523049     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00763-7     Document Type: Article

References (16)

1. Carroll, F. I.; Lewin, A. H.; Abraham, P.; Parham, K.; Boja, J. W.; Kuhar, M. J. J. Med. Chem. 1991, 34, 883-886.
2. Carroll, F. I.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. J. Med. Chem.. 1992, 34, 969-981 and references cited therein.
3. Simoni, D.; Roberti, M.; Andrisano, V.; Manferdini, M.; Rondanin, R.; Kozikowski, A. P. J. Org. Chem. 1998, 63, 4834-4838.
4. Simoni, D.; Stoelwinder, J.; Kozikowski, A. P.; Johnson, K. M.; Bergman, J. S.; Ball, R. G. J. Med. Chem. 1993, 36, 3975-3978.
5. Brownbridge, P.; Chan, T.-H. Tetrahedron Lett. 1979, 4437-4440.
6. Kainz, A.; Eiden, F. Arch. Pharm. (Weinhein) 1990, 323, 191-194.
7. Meltzer, P. C; Liang, A. Y.; Blundell, P.; Gonzalez, M. D.; Chen, Z.; George, C.; Madras, B. K. J. Med. Chem. 1997, 40, 2661-2673.
8. Shirai, R.; Tanaka, M.; Koga, K. J. Am. Chem. Soc. 1986, 108, 543-545.
9. Shirai, R.; Aoki, K.; Sato, D.; Kim, H.-D.; Murakata, M.; Yasukata, T.; Koga, K. Chem. Pharm. Bull. 1994, 42, 690-695.
10. Cain C. M.; Cousins, R. P. C.; Coumbarides, G.; Simpkins, N. S. Tetrahedron. 1990, 46, 523-544.
11. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry. 1991, 2, 1-26.
12. Bunn, B. J.; Cox, P. J.; Simpkins, N. S. Tetrahedron. 1993, 49, 207-218.
13. Majewski, M.; Lazny, R. J. Org. Chem. 1995, 60, 5825-5830 and references cited therein.
14. O'Brien P. J. Chem. Soc., Perkin Trans, 1 1998, 1439-1447.
15. 3), 83 % ee.
16. Nowakowski, M.; Hoffmann, H. M. R. Tetrahedron Lett. 1997, 38, 1001. These authors have proposed the preparation of a 6,7-dehydro analog of 7 using the HCLA methodology.