A five-step synthesis of (S)-macrostomine from (S)-nicotine

Organic Letters

Volumn 12, Issue 20, 2010, Pages 4513-4515

  Enamorado, Monica F ^a   Ondachi, Pauline W ^a   Comins, Daniel L ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE; MACROSTOMINE; NICOTINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ISOQUINOLINES; MOLECULAR STRUCTURE; NICOTINE;

EID: 77957851355     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101887b     Document Type: Article

References (46)

1. Mnatsakanyan, V. A.; Preininger, V.; Simanek, V.; Klasek, A.; Dolejs, L.; Santavy, F. Tetrahedron Lett. 1974, 10, 851-852
2. Israilov, I. S.; Manushakyan, M. A.; Mnatsakanyan, V. A.; Yusunov, M. S. Chem. Nat. Compd. 1984, 20, 71-73
3. Mnatsakanyan, V. A.; Preininger, V.; Simanek, V.; Jurina, J.; Klasek, A.; Dolejs, L.; Santavy, F. Collect. Czech. Chem. Commun. 1977, 42, 1421-1430
4. Müller-Schweinitzer, E.; Hasse, J.; Swoboda, L. J. Asthma 1993, 30, 451-457
5. Siuciak, J. A.; Chapin, D. S.; Harms, J. F.; Lebel, L. A.; McCarthy, S. A.; Chambers, L.; Shrikhande, A.; Wong, S.; Menniti, F. S.; Schmidt, C. J. Neuropharmacol. 2006, 51, 386-396
6. Tang, Y.; Luan, J.; Zhang, X. Plast. Reconstr. Surg. 2004, 114, 1166-1169
7. Wykypiel, W.; Seebach, D. Tetrahedron Lett. 1980, 21, 1927-1930
8. Wiegrebe, W.; Mahboobi, S.; Dannhardt, G.; Mayer, K.; Eibler, E. Chimia 1981, 35, 288-289
9. Sharma, R. B.; Kapil, R. S. Indian J. Chem. 1982, 21B, 141-143
10. Brunner, H.; Kurzinger, A.; Mahboobi, S.; Wiegrebe, W. Arch. Pharm. (Weinheim). 1988, 321, 73-76
11. Mahboobi, S.; Wiegrebe, W. Arch. Pharm. (Weinheim). 1991, 324, 275-281
12. Comins, D. L.; King, L. S.; Smith, E. D.; Fevrier, F. C. Org. Lett. 2005, 7, 5059-5062
13. Fevrier, F. C.; Smith, E. D.; Comins, D. L. Org. Lett. 2005, 7, 5457-5460
14. Smith, E. D.; Fevrier, F. C.; Comins, D. L. Org. Lett. 2006, 8, 179-182
15. Wagner, F. F.; Comins, D. L. Eur. J. Org. Chem. 2006, 16, 3562-3565
16. Wagner, F. F.; Comins, D. L. Tetrahedron 2007, 63, 8065-8082
17. Capracotta, S. S.; Comins, D. L. Tetrahedron Lett. 2009, 50, 1806-1808
18. Ondachi, P. W.; Comins, D. L. Tetrahedron Lett. 2008, 49, 569-572
19. Ondachi, P. W.; Comins, D. L. J. Org. Chem. 2010, 75, 1706-1716
20. Wagner, F. F.; Comins, D. L. Org. Lett. 2006, 8, 3549-3552
21. Wagner, F. F.; Comins, D. L. J. Org. Chem. 2006, 71, 8673-8675
22. Comins, D. L.; Smith, E. D. Tetrahedron Lett. 2006, 47, 1449-1451
23. Connon, S. J.; Hegarty, A. F. J. Chem. Soc., Perkin Trans. I 2000, 1245-1249
24. Zoltewicz, J. A.; Smith, C. L. Tetrahedron 1969, 25, 4331-4337
25. Cook, J. D.; Wakefield, B. J. J. Chem. Soc. C 1969, 1973-1978
26. Lin, W.; Chen, L.; Knochel, P. Tetrahedron 2007, 63, 2787-2797
27. Walters, M. A.; Shay, J. J. Synth. Commun. 1997, 27, 3573-3579
28. Carroll, F. I.; Robinson, T. P.; Brieaddy, L. E.; Atkinson, R. N.; Mascarella, S. W.; Damaj, M. I.; Martin, B. R.; Navarro, H. A. J. Med. Chem. 2007, 50, 6383-6391
29. Gros, P.; Fort, Y.; Caubere, P. J. Chem. Soc., Perkin Trans. 1 1997, 20, 3071-3080
30. Gros, P.; Fort, Y.; Caubere, P. J. Chem. Soc., Perkin Trans. 1 1997, 24, 3597-3600
31. Choppin, S.; Gros, P.; Fort, Y. Org. Lett. 2000, 2, 803-805
32. Gros, P.; Choppin, S.; Mathieu, J.; Fort, Y. J. Org. Chem. 2002, 67, 234-237
33. Bothner-By, A. A.; Harris, R. K. J. Am. Chem. Soc. 1965, 87, 3451-3455
34. McDonald, E.; Suksamrarn, A.; Wylie, R. D. J. Chem. Soc., Perkin Trans. 1 1979, 1893-1900
35. Ondachi, P. W. Synthesis of Alkoxy, Heterocyclic and Fused-Rings Derivatives of (S)-Nicotine from Natural Nicotine, Progress towards the total Synthesis of (S)-Macrostomine, Ph.D. Dissertation, North Carolina State University, Raleigh, NC, 2008.
36. Iten, P. X.; Hofmann, A. A.; Eugster, C. H. Helv. Chim. Acta 1978, 61, 430-443
37. Chen, Z.; Muller, P.; Swager, T. M. Org. Lett. 2006, 8, 273-276
38. Hart, H.; Bashir-Hashemi, A.; Luo, J.; Meador, M. A. Tetrahedron 1986, 42, 1641-1654
39. Bailly, F.; Cottet, F.; Schlosser, M. Synthesis 2005, 5, 791-797
40. Pons, J. M.; Santelli, M. Tetrahedron 1990, 46, 513-522
41. Bharati, P.; Comins, D. L. Org. Lett. 2008, 10, 221-223
42. Corriu, R. J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 144
43. Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374-4376
44. Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958-1969
45. Ibuki, E.; Ozasa, S.; Fujioka, Y.; Okada, M.; Terada, K. Bull. Chem. Soc. Jpn. 1980, 53, 821-822
46. Kumada, M. Pure Appl. Chem. 1980, 52, 669-679