Total synthesis of 8,14-dihydromorphinandienone alkaloids

Organic Letters

Volumn 16, Issue 6, 2014, Pages 1708-1711

  Ghavimi, Bahman ^a   Magnus, Philip ^a  

^a University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMINE; MORPHINAN DERIVATIVE; SINOMENINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; AMINES; HYDROGENATION; MOLECULAR STRUCTURE; MORPHINANS; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 84897016293     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500368p     Document Type: Article

References (69)

1. Kutchan, T. M. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Academic Press: London, 1998; Vol. 50, p 257.
2. Barton, D. H. R.; Cohen, T. Festschrift Arthur Stoll; Birkhauser: Basel, 1957, 117.
3. Barton, D. H. R.; Kirby, G. W.; Steglich, W.; Thomas, G. M. Proc. Chem. Soc. 1963, 203
4. Haynes, L. J.; Stuart, K. L. J. Chem. Soc. 1963, 1784
5. Haynes, L. J.; Husbands, G. E. M.; Stuart, K. L. J. Chem. Soc. C 1968, 951
6. Haynes, L. J.; Husbands, G. E. M.; Stuart, K. L. Chem. Commun. 1967, 15
7. Stuart, K. L.; Woo-Ming, R. B. Phytochemistry 1969, 8, 777
8. Mukhtar, M. R.; Hadi, A. H. A.; Litaudon, M.; Awang, K. Fitoterapia 2004, 75, 792
9. Wei, Y.; Jin, Q. Zhongguo Yaolixue Tongbao 1997, 13, 180
10. Sasaki, Y.; Ueda, S. Yakugaku, Zasshi 1958, 78, 44
11. Sasaki, Y.; Ueda, S. Yakugaku, Zasshi 1963, 83, 418
12. Barton, D. H. R.; Kirby, A. J.; Kirby, G. W. J. Chem. Soc. (C) 1968, 929
13. Okabe, K.; Kunio, H.; Sawa, Y. K. Chem. Pharm. Bull. 1968, 16, 1611
14. Melo, P. S.; Cavalcante, H. M. M.; Barbosa-Filho, J. M.; Diniz, M. F. F. M.; de Medeiros, I. A.; Haun, M. Toxicol. Lett. 2003, 142, 143
15. Cavalcante, H. M. M.; Riberio, T. P.; Silva, D. F.; Nunes, X. P.; Barbosa-Filho, J. M.; Diniz, M. F. F. M.; Correia, N. A.; Braga, V. A.; Medeiros, I. A. Basic & Clinical Pharmacology & Toxicology 2010, 108, 122
16. Freitas, M. R.; Alencar, J. L.; Da-Cunha, E. V. L; Barbosa-Filho, J. M.; Gray, A. I. Phytochemistry 1995, 40, 1553
17. Vecchietti, V.; Casagrande, C.; Ferrari, G. Tetrahedron Lett. 1976, 19, 1631
18. Vecchietti, V.; Casagrande, C.; Ferrari, G.; Danieli, B.; Palmisano, G. J. Chem. Soc., Perkin Trans. 1 1981, 578
19. Ludwig, W.; Schafer, H. J. Angew. Chem., Int. Ed. Engl. 1986, 25, 1025
20. Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030
21. Szantay, C.; Blasko, G.; Barczai-Beke, M.; Pechy, P.; Dornyei, G. Tetrahedron Lett. 1980, 21, 3509
22. Szantay, C.; Barczai-Beke, M.; Pechy, P.; Blasko, G.; Dornyei, G. J. Org. Chem. 1982, 47, 594
23. Zenk, M. H.; Gerardy, R.; Stadler, R. J. Chem. Soc., Chem. Commun. 1989, 1725
24. Wiegand, S.; Schafer, H. J. Tetrahedron 1995, 51, 5341
25. Udvardy, A.; Sipos, A. Cent. Eur. J. Chem. 2013, 11, 2022
26. Henry, L. C. R. Acad. Sci. Ser. C 1895, 1265
27. Henry, L. Bull. Soc. Chim. Fr. 1895, 13, 999
28. Luzzio, F. A. Tetrahedron 2001, 57, 915
29. Magnus, P.; Sane, N.; Fauber, B. P.; Lynch, V. J. Am. Chem. Soc. 2009, 131, 16045
30. Ono, N. The Nitro Group in Organic Synthesis; Wiley: New York, 2001.
31. Kabalka, G. W.; Varma, R. S. Org. Prep. Proced. Int. 1987, 19, 283
32. Posner, G. H. Angew. Chem., Int. Ed. Engl. 1978, 17, 487
33. Jiang, T.; Gao, H.; Han, B.; Zhao, G.; Chang, Y.; Wu, W.; Gao, L.; Yang, G. Tetrahedron Lett. 2004, 45, 2699
34. Dandia, A.; Jain, A. K.; Sharma, S. Tetrahedron Lett. 2012, 53, 5859
35. Yi, B.; Zhang, Y.; Zhang, R.; Dang, L.; Yang, H.; Qiu, M. Adv. Sci. Lett. 2012, 10, 375
36. Greaves, T. L.; Drummond, C. J. Chem. Rev. 2008, 108, 206
37. Parvulescu, V. I.; Hardacre, C. Chem. Rev. 2007, 107, 2615
38. Ballini, R.; Bosica, G.; Forconi, P. Tetrahedron 1996, 52, 1677
39. Ballini, R.; Bosica, G. J. Org. Chem. 1994, 59, 5466
40. Ballini, R.; Barboni, L.; Palmieri, A. Synlett. 2007, 19, 3019
41. Ballini, R.; Bosica, G.; Fiorin, D.; Palmieri, A.; Petrini, M. Chem. Rev. 2005, 105, 933
42. Vivek, J.; Bulbule, G. K.; Jnaneshwara, R. R. D.; Hanumant, B. B.; Vishnu, H. D. Synth. Commun. 2001, 31, 3623
43. Gomez-Bengoa, E.; Linden, A.; Lopez, R.; Mugica-Mendiola, I.; Oiarbide, M.; Palomo, C. J. Am. Chem. Soc. 2008, 130, 7955
44. Maruoka, K. Org. Process Res. Dev. 2008, 12, 679
45. Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts; Ishikawa, T., Ed.; Wiley: New York, 2009.
46. Caubere, P. Chem. Rev. 1993, 93, 2317
47. Gund, P. J. J. Chem. Educ. 1972, 49, 100
48. Gobi, A.; Frenking, G. J. Am. Chem. Soc. 1993, 115, 2363
49. Raczynska, E. D.; Cyranski, M. K.; Gutowski, M. J. Phys. Org. Chem. 2003, 16, 91
50. Leminger, O. Chem. Prum. 1972, 22, 553
51. Gowda, D.; Mahesh, B.; Shankare, G. Ind. J. Chem. Sect. B 2001, 40, 75
52. Gowda, S.; Gowda, B. K. K.; Gowda, D. C. Synth. Commun. 2003, 33, 281
53. Pitts, M. R.; Harrison, J. R.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 2001, 9, 955
54. Banik, B. K.; Suhendra, M.; Banik, I.; Becker, F. F. Synth. Commun. 2000, 30, 3745
55. Gamble, A. B.; Garner, J.; Gordon, C. P.; O'Conner, S. M. J.; Keller, P. A. Synth. Commun. 2007, 37, 2777
56. Gabriele, B.; Salerno, G.; Veltri, L.; Costa, M.; Massera, C. Eur. J. Org. Chem. 2001, 4607
57. Abiraj, K.; Gowda, S.; Gowda, D. C. Synth. React. Inorg. Met.-Org. Chem. 2002, 32, 1409
58. Ram, S.; Ehrenkanfer, R. E. Tetrahedron Lett. 1984, 25, 3415
59. Kabalka, G. W.; Pace, R. D.; Wadgaonkar, P. P. Synth. Commun. 1990, 20, 2453
60. Gowda, D. C.; Gowda, A. S. P.; Baba, A. R.; Gowda, S. Synth. Commun. 2000, 30, 2889
61. Yuste, F.; Saldana, M.; Walls, F. Tetrahedron Lett. 1982, 23, 147
62. Eschweiler, W. Ber. 1905, 38, 880
63. Clark, H. T.; Gillespie, H. B.; Weisshaus, S. Z. J. Am. Chem. Soc. 1933, 55, 4571
64. Moore, M. L. Org. React. 1949, 5, 301
65. Frakas, E.; Sunman, C. J. J. Org. Chem. 1985, 50, 1110
66. Barton, D. H. R.; Kirby, G. W.; Steglich, W.; Thomas, G. M.; Battersby, A. R.; Dobson, T. A.; Ramuz, H. J. Chem. Soc. 1965, 2423
67. Schopf, C.; Hirsch, H. Annalen 1913, 489, 224
68. Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109
69. Barber, R. B.; Rapoport, H. J. Med. Chem. 1976, 19, 1175