A direct and general method for the reductive alkylation of tertiary lactams/amides: Application to the step economical synthesis of alkaloid (-)-morusimic acid D

Journal of Organic Chemistry

Volumn 78, Issue 17, 2013, Pages 8305-8311

  Xiao, Kai Jiong ^a   Wang, Yu ^a   Huang, Ying Hong ^a   Wang, Xiao Gang ^a   Huang, Pei Qiang ^a,b  

^a XIAMEN UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC HYDROGENATION; DIASTEREO-SELECTIVITY; GRIGNARD REAGENT; ITS APPLICATIONS; PIPERIDINE ALKALOIDS; REDUCING CONDITIONS; REDUCTIVE ALKYLATION; STEREOSELECTIVE SYNTHESIS;

ALKALOIDS; ALKYLATION; HYDROGENATION; METABOLITES; NITROGEN COMPOUNDS; STEREOCHEMISTRY; STEREOSELECTIVITY;

AMIDES;

ALIPHATIC AMINE; ALKALOID DERIVATIVE; ALKYL GROUP; ALUMINUM DERIVATIVE; AMIDE; BENZYL DERIVATIVE; ESTER DERIVATIVE; IMINE; LACTAM DERIVATIVE; LITHIUM DERIVATIVE; MORUSIMIC ACID D; PALLADIUM COMPLEX; PIPERIDINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRROLIDINE DERIVATIVE; REDUCING AGENT; SODIUM DERIVATIVE; TIN DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; DIASTEREOISOMER; GRIGNARD REACTION; HYDROGENATION; ONE POT SYNTHESIS; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

ALKYLATION; AMIDES; LACTAMS; MOLECULAR STRUCTURE; PIPERIDINES; STEREOISOMERISM;

EID: 84883804882     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4007656     Document Type: Article

References (82)

1. Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic: San Diego, CA, 1993; Vol. 44, Chapter 3.
2. Schneider, M. Pyridine and Piperidine Alkaloids: An Update. In Alkaloids: Chemical and Biochemical Perspectives; Pelletier, S. W., Ed.; Elsevier Science: Oxford, U.K., 1996; Vol. 10, pp 155-299.
3. Daly, J. W.; Spande, T. F.; Garraffo, H. M. J. Nat. Prod. 2005, 68, 1556-1575
4. Michael, J. P. Nat. Prod. Rep. 2008, 25, 139-165
5. Liddell, J. R. Nat. Prod. Rep. 2002, 19, 773-781
6. O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435-446 and previous reviews in the respective series
7. Rakba, N.; Melhaoui, A.; Rissel, M.; Morel, I.; Loyer, P.; Lescoat, G. Toxicon 2000, 38, 1389-1402
8. Melhaoui, A.; Mallea, M.; Jossang, A.; Bodo, B. Nat. Prod. Lett. 1993, 2, 237-242
9. Schwartz, R. E.; Liesch, J.; Hensens, O.; Zitano, L.; Honeycutt, S.; Garrity, G.; Fromtling, R. A.; Onishi, J.; Monaghan, R. J. Antibiot. 1988, 41, 1774-1779
10. Johnson, J. H.; Phillipson, D. W.; Kahle, A. D. J. Antibiot. 1989, 42, 1184-1185
11. López, T. A.; Cid, M. S.; Bianchini, M. L. Toxicon 1999, 37, 841-865
12. Sansores-Peraza, P.; Rosado-Vallado, M.; Brito-Loeza, W.; Mena-Rejón, G. J.; Quijano, L. Fitoterapia 2000, 71, 690-692
13. Kusano, G.; Orihara, S.; Tsukamoto, D.; Shibano, M.; Coskun, M.; Guvenc, A.; Erdurak, C. S. Chem. Pharm. Bull. 2002, 50, 185-192
14. Husson, H. P.; Royer, J. Chem. Soc. Rev. 1999, 28, 383
15. Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843-9873
16. Joseph, S.; Comins, D. Curr. Opin. Drug Discovery Dev. 2002, 5, 870-880
17. Toyooka, N.; Nemoto, H. Synthetic Studies on Biologically Active Alkaloids Starting from Lactam-Type Chiral Building Blocks. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 2003; Vol. 29, pp 419-448.
18. Huang, P.-Q. Synlett 2006, 1133-1149
19. Escolano, C.; Amat, M.; Bosch, J. Chem.-Eur. J. 2006, 12, 8198-8207
20. Koulocheri, S. D.; Pitsinos, E. N.; Haroutounian, S. A. Curr. Org. Chem. 2008, 12, 1454-1467
21. Wijdeven, M. A.; Willemsen, J.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 2010, 2831-2844
22. Merino, P.; Tejero, T.; Greco, G.; Marca, E.; Delso, I.; Gómez-SanJuan, A.; Matute, R. Heterocycles 2012, 84, 75-100
23. Cochi, A.; Pardo, D. G.; Cossy, J. Heterocycles 2012, 86, 89-116
24. Randl, S.; Blechert, S. J. Org. Chem. 2003, 68, 8879-8882
25. Pu, X. T.; Ma, D. W. Angew. Chem., Int. Ed. 2004, 43, 4222-4225
26. Leverett, C. A.; Cassidy, M. P.; Padwa, A. J. Org. Chem. 2006, 71, 8591-8601
27. Coombs, T. C.; Lee, M. D.; Wong, H.; Armstrong, M.; Cheng, B.; Chen, W.; Moretto, A. F.; Liebeskind, L. S. J. Org. Chem. 2008, 73, 882-888
28. Shengule, S. R.; Willis, A.; Pyne, S. G. Tetrahedron 2012, 68, 1207-1215
29. Liotta, D.; Saindane, M.; Sunay, U.; Jamison, W. C. L.; Grossman, J.; Phillips, P. J. Org. Chem. 1985, 50, 3243-3245
30. Watanabe, Y.; Iida, H.; Kibayashi, C. J. Org. Chem. 1989, 54, 4088-4097
31. Comins, D. L.; Zheng, X.; Goehring, R. R. Org. Lett. 2002, 4, 1611-1613
32. Shibagaki, M.; Matsushita, H.; Kaneko, H. Heterocycles 1986, 24, 2315-2319
33. Micouin, L.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1996, 37, 849-852
34. Sancibrao, P.; Karila, D.; Kouklovsky, C.; Vincent, G. J. Org. Chem. 2010, 75, 4333-4336
35. Hwang, Y. C.; Chu, M.; Fowler, F. W. J. Org. Chem. 1985, 50, 3885-3890
36. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 1719-1722
37. Suh, Y.-G.; Kim, S.-A.; Jung, J.-K.; Shin, D.-Y.; Min, K.-H.; Koo, B.-A.; Kim, H.-S. Angew. Chem., Int. Ed. 1999, 38, 3545-3547
38. Amat, M.; Llor, N.; Hidalgo, J.; Escolano, C.; Bosch, J. J. Org. Chem. 2003, 68, 1919-1928
39. Shirokane, K.; Kurosaki, Y.; Sato, T.; Chida, N. Angew. Chem., Int. Ed. 2010, 49, 6369-6372
40. Vincent, G.; Guillot, R.; Kouklovsky, C. Angew. Chem., Int. Ed. 2011, 50, 1350-1353
41. Oda, Y.; Sato, T.; Chida, N. Org. Lett. 2012, 14, 950-953
42. Shiosaki, K.; Rapoport, H. J. Org. Chem. 1985, 50, 1229-1239
43. Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. J. Am. Chem. Soc. 1989, 111, 2588-2595
44. Toyooka, N.; Yoshida, Y.; Yotsui, Y.; Momose, T. J. Org. Chem. 1999, 64, 4914-4919
45. Schär, P.; Renaud, P. Org. Lett. 2006, 8, 1569-1571
46. Murai, T.; Toshio, R.; Mutoh, Y. Tetrahedron 2006, 62, 6312-6320
47. Mitamura, T.; Ogawa, A. Org. Lett. 2009, 11, 2045-2048
48. Murai, T.; Mutoh, Y. Chem. Lett. 2012, 41, 2-8
49. Giovannini, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1989, 54, 228-234
50. Yoda, H.; Yamazaki, H.; Kawauchi, M.; Takabe, K. Tetrahedron: Asymmetry 1995, 6, 2669-2672
51. Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583-4592
52. Brenneman, J. B.; Machauer, R.; Martin, S. F. Tetrahedron 2004, 60, 7301-7314
53. Kropf, J. E.; Meigh, I. C.; Bebbington, M. W. P.; Weinreb, S. M. J. Org. Chem. 2006, 71, 2046-2055
54. Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817-3856
55. Yazici, A.; Pyne, S. G. Synthesis 2009, 339-368
56. Yazici, A.; Pyne, S. G. Synthesis 2009, 513-541
57. Cuny, G. D.; Buchwald, S. L. Synlett 1995, 519-522 (N, O -acetals)
58. Wijdeven, M. A.; van Delft, F. L.; Rutjes, F. P. J. T. Tetrahedron 2010, 66, 5623-5636 (N, O -acetals)
59. Brown, D. S.; Clarreau, P.; Hansson, T.; Ley, S. V. Tetrahedron 1991, 47, 1311-1328 (N-α -phenylsulphonyl derivatives)
60. Suh, Y. G.; Shin, D. Y.; Jung, J. K.; Kim, S. H. Chem. Commun. 2002, 1064-1065 (N, O -acetals)
61. Neipp, C. E.; Martin, S. F. J. Org. Chem. 2003, 68, 8867-8878
62. Madan, S.; Milano, P.; Eddings, D. B.; Gawley, R. E. J. Org. Chem. 2005, 70, 3066-3071 (N -α-Bt derivatives)
63. For transformations via N-t -butyl formamidines, see: Gottlieb, L.; Meyers, A. I. Tetrahedron Lett. 1990, 31, 4723-4726
64. Ha, J. D.; Cha, J. K. J. Am. Chem. Soc. 1999, 121, 10012-10020
65. Toyooka, N.; Nemoto, H. Tetrahedron Lett. 2003, 44, 569-570
66. Liao, J.-C.; Xiao, K.-J.; Zheng, X.; Huang, P.-Q. Tetrahedron 2012, 68, 5297-5302 and references cited therein
67. Xiao, K.-J.; Luo, J.-M.; Ye, K.-Y.; Wang, Y.; Huang, P.-Q. Angew. Chem., Int. Ed. 2010, 49, 3037-3040
68. Lin, G.-J.; Zheng, X.; Huang, P.-Q. Chem. Commun. 2011, 47, 1545-1547
69. Xiao, K.-J.; Wang, Y.; Ye, K.-Y.; Huang, P.-Q. Chem.-Eur. J. 2010, 16, 12792-12796
70. Xiao, K.-J.; Wang, A.-E; Huang, Y.-H.; Huang, P.-Q. Acta Chim. Sin. 2012, 70, 1917-1922
71. Stang, P. J.; Warren, T. Synthesis 1980, 283-284
72. Harder, I.; Hanack, M. Chem. Ber. 1984, 117, 3004-3020
73. Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1983, 85-126
74. Baraznenok, I. L.; Nenajdenko, V. G.; Balenkova, E. S. Tetrahedron 2000, 56, 3077-3119
75. Bélanger, G.; Larouche-Gauthier, R.; Ménard, F.; Nantel, M.; Barabé, F. J. Org. Chem. 2006, 71, 704-712 and references cited therein
76. During the submission of this manuscript, a paper highlighting recent advancements on the chemoselective activation strategies of amidic carbonyls towards nucleophilic reagents appeared: Pace, V.; Holzer, W. Aust. J. Chem. 2013, 66, 507-510
77. Breña-Valle, L. J.; Sánchez, R. C.; Cruz-Almanza, R. Tetrahedron: Asymmetry 1996, 7, 1019-1026
78. Yu, D.-S.; Xu, W.-X.; Liu, L.-X.; Huang, P.-Q. Synlett 2008, 1189-1192
79. Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856-5858
80. Taber, D. F.; Silverberg, L. J. Tetrahedron Lett. 1991, 32, 4227-4230
81. Ashton, P. R.; Koniger, R.; Stoddart, J. F. J. Org. Chem. 1996, 61, 903-908
82. Love, B. E.; Jones, E. G. J. Org. Chem. 1999, 64, 3755-3756