Enantioselective syntheses of both enantiomers of cis-pyrrolidine 225H

Tetrahedron

Volumn 66, Issue 25, 2010, Pages 4428-4433

  Shu, Hong ^a   Noble, April R ^a   Zhang, Suhong ^a   Miao, Lei ^a   Trudell, Mark L ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

Amphibian alkaloids; Ant venom alkaloids; Enantioselective synthesis; Pyrrolidine

Indexed keywords

(1R,2R,3S,5S) 3 (BENZOYLOXY) 2 METHOXYCARBONYL 8 ETHOXY CARBONYL 8 AZABICYCLO[3.2.1]OCTANE; (1R,5S) 8 BENZYLOXYCARBONYL 2 (TERT BUTYL DIMETHYLSILYLOXY) 8 AZABICYCLO[3.2.1]OCT 2 ENE; (1R,5S) 8 BENZYLOXYCARBONYL 8 AZABICYCLO[3.2.1]OCTAN 2 ONE; (1R,5S) 8 ETHOXYCARBONYL 8 AZABICYCLO[3.2.1]OCTAN 2 ONE; (2R,5S) 1 BENZYLOXYCARBONYL 2 (HEX 2 ENYL) 5 (1 PENTYL)PYRROLIDINE; (2R,5S) 1 BENZYLOXYCARBONYL 2 (HEX 2 ENYL) 5 (PENT 2 ENYL)PYRROLIDINE; (2R,5S) 1 BENZYLOXYCARBONYL 2 METHOXYCARBONYL 5 (2 HYDROXYETHYL)PYRROLIDINE; (2R,5S) 1 BENZYLOXYCARBONYL 2 METHOXYCARBONYL 5 (2 OXOETHYL)PYRROLIDINE; (2R,5S,Z) 1 BENZYLOXYCARBONYL 2 METHOXY CARBONYL 5 (PENT 2 ENYL)PYRROLIDINE; (2R,5S,Z) 1 BENZYLOXYCARBONYL 2 METHOXYCARBONYL 5 (HEX 2 ENYL)PYRROLIDINE; AZABICYCLO DERIVATIVE; CIS 2,5 PYRROLIDINE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

AMPHIBIA;

EID: 77953121139     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.037     Document Type: Article

References (39)

1. Daly J.W., Garraffo H.M., and Spande T.F. J. Nat. Prod. 68 (2005) 1556-1575
2. Daly J.W. J. Med. Chem. 46 (2003) 445-452
3. Daly J.W. In: Cordell G.A. (Ed). The Alkaloids Vol. 50 (1998), Academic, New York, NY 141-169
4. Daly J.W., Garraffo H.M., and Spande T.F. In: Cordell G.A. (Ed). The Alkaloids Vol. 43 (1993), Academic, New York, NY 186-188
5. Jones T.H., Blum M.S., and Fales H.M. Tetrahedron 38 (1982) 1949-1958
6. Numata A., and Ibuka T. In: Brossi A. (Ed). The Alkaloids Vol. 31 (1987), Academic, New York, NY 193-315
7. Jones T.H., DeVries P.J., and Escoubas P. J. Chem. Ecol. 17 (1991) 2507-2517
8. Jones T.H., Gorman J.S.T., Snelling R.R., Delabie J.H.C., Blum M.S., Garraffo H.M., Jain P., Daly J.W., and Spande T.F. J. Chem. Ecol. 25 (1999) 1179-1193
9. Jones T.H., Zottig V.E., Robertson H.G., and Snelling R.R. J. Chem. Ecol. 29 (2003) 2721-2727
10. Jones T.H., Voegtle H.L., Miras H.M., Weatherford R.G., Spande T.F., Garraffo H.M., Daly J.W., Davidson D.W., and Snelling R.R. J. Nat. Prod. 70 (2007) 160-168
11. Daly J.W., Whittaker N., Spande T.F., Highet R.J., Feigl D., Nishimori N., Tokuyama T., and Meyers C.W. J. Nat. Prod. 49 (1986) 265-280
12. Daly J.W., Secunda S.I., Garraffo H.M., Spande T.F., Wisnieski A., and Cover J.F. Toxicon 32 (1994) 657-663
13. For example syntheses of trans-2,5-pyrrolidines, see. Gribkov D.V., Hultzsch K.C., and Hampel F. J. Am. Chem. Soc. 128 (2006) 3748-3759
14. Davis F.A., Song M., and Augustine A. J. Org. Chem. 71 (2006) 2779-2786
15. Vasse J.-L., Joosten A., Denhez C., and Szymoniak J. Org. Lett. 7 (2005) 4887-4889
16. Ryu J.S., Marks T.J., and McDonald F.E. Org. Lett. 3 (2001) 3091-3094
17. Katritzky A.R., Cui X.-L., Yang B., and Steel P.J. J. Org. Chem. 64 (1999) 1979-1985
18. Arredondo V.M., Tan S., McDonald F.E., and Marks T.J. J. Am. Chem. Soc. 121 (1999) 3633-3639
19. Celimene C., Dhimane H., and Lhommet G. Tetrahedron 54 (1998) 10457-10468
20. Bloch R., Brillet-Fermandez C., and Mandville G. Tetrahedron: Asymmetry 5 (1994) 745-750
21. Machinaga N., and Kibayashi C. J. Org. Chem. 56 (1991) 1386-1393
22. Bäckvall J.E., Schink H.E., and Renko Z.D. J. Org. Chem. 55 (1990) 826-831
23. Takahata H., Takehara H., Ohkubo N., and Momose T. Tetrahedron: Asymmetry 1 (1990) 561-566
24. Gessner W., Takahashi K., Brossi A., Kowalski M., and Kaliner M.A. Helv. Chim. Acta 70 (1987) 2003-2010
25. Jones T.H., Blum M., Murray S., and Fales H.M. Tetrahedron Lett. 12 (1979) 1031-1034
26. For a recent reviews of pyrrolidine and related alkaloid synthesis see:
27. Michael J.P. Nat. Prod. Rep. 21 (2004) 625-649
28. Cheng Y., Huang Z.-T., and Wang M.-X. Curr. Org. Chem. 8 (2004) 325-351
29. Pyne S.G., Davis A.S., Gates N.J., Hartley J.P., Lindsay K.B., Machan T., and Tang M. Synlett (2004) 2670-2680
30. Michael J.P. Alkaloids 55 (2001) 91-258
31. For example syntheses of cis-2,5-pyrrolidines, see. Raziullah S., and Moloney M.G. Org. Biomol. Chem. 4 (2006) 2600-2615
32. Llamas T., Gomez R.A., and Carretero J.C. Org. Lett. 8 (2006) 1795-1798
33. Pandey G., Reddy P.Y., and Bhalerao U.T. Tetrahedron Lett. 32 (1991) 5147-5150
34. Zhang S., Xu L., Miao L., Shu H., and Trudell M.L. J. Org. Chem. 72 (2007) 3133-3136
35. Zhang C., Lomenzo S.A., Ballay C., and Trudell M.L. J. Org. Chem. 62 (1997) 7888-7889
36. Lomenzo S.A., Enmon J., Troyer M.C., and Trudell M.L. Synth. Commun. 25 (1995) 3681-3690
37. Confiscated grade (-)-cocaine hydrochloride was provided by NIDA Drug Supply System, Research Technology Branch, National Institute on Drug Abuse. A DEA Schedule II license was required.
38. Ravard A., and Crooks P.A. Chirality 8 (1996) 295-299
39. Miao L., DiMaggio S., Shu H., and Trudell M.L. Org. Lett. 11 (2009) 1579-1582