π-Allyl palladium approach toward the diazabicyclo[3.2.1]octane core of the naphthyridinomycin alkaloids

Tetrahedron

Volumn 62, Issue 45, 2006, Pages 10507-10517

  Woo, Grace H C ^a   Kim, Se Ho ^a   Wipf, Peter ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; BICYCLO[3.2.1]OCTANE DERIVATIVE; PALLADIUM COMPLEX;

ALKYLATION; ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 33748966857     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.06.114     Document Type: Article

References (73)

1. Arai T., and Kubo A. In: Brossi A. (Ed). The Alkaloids Vol. 21 (1983), Academic, New York, NY 55
2. Remers W.A. The Chemistry of Antitumor Antibiotics Vol. 2 (1988), Wiley, New York, NY p 93
3. Remers W.A. The Chemistry of Antitumor Antibiotics Vol. 2 (1988), Wiley, New York, NY p 120
4. Arai T. In: Wagman G.H., and Cooper R. (Eds). Journal of Chromatography Library: Natural Product Isolation Vol. 43 (1989), Elsevier, New York, NY 191
5. Kubo A., and Saito N. Studies in Natural Products Chemistry Vol. 10 (1992), Elsevier, New York, NY p 77
6. Fukuyama T. In: Pearson W. (Ed). Advances in Heterocyclic Natural Product Synthesis Vol. 2 (1992), JAI, Greenwich, CT 189-249
7. Katoh T., and Terashima S. Studies in Natural Products Chemistry Vol. 19 (1997), Elsevier, New York, NY p 289
8. Ozturk T. In: Brossi A. (Ed). The Alkaloids Vol. 53 (2000), Academic, New York, NY 119
9. Rinehart K.L. Med. Res. Rev. 20 (2000) 1
10. Scott J.D., and Williams R.M. Chem. Rev. 102 (2002) 1669
11. Tanida S., Hasegawa T., Muroi M., and Higashida E. J. Antibiot. 33 (1980) 1443
12. Muroi M., Tanida S., Asai M., and Kishi T. J. Antibiot. 33 (1980) 1449
13. Tanida S., Izawa M., and Hasegawa T. J. Antibiot. 34 (1981) 489
14. Hida T., Muroi M., Tanida S., and Harada S. J. Antibiot. 47 (1994) 917
15. Tanida S., Hasegawa T., and Yoneda M. Antimicrob. Agents Chemother. 22 (1982) 735
16. Horiguchi T., Nishi K., Hakoda S., Tanida S., Nagata A., and Okayama H. Biochem. Pharmacol. 48 (1994) 2139
17. Eckstein J.W. Invest. New Drugs 18 (2000) 149
18. Wipf P., Hopkins C.R., Phillips E.O., and Lazo J.S. Tetrahedron 58 (2002) 6367
19. See Ref. 1f;
20. Herberich B., Kinugawa M., Vazquez A., and Williams R.M. Tetrahedron Lett. 42 (2001) 543
21. Scott J.D., and Williams R.M. J. Am. Chem. Soc. 124 (2002) 2951
22. Jin W., Metobo S., and Williams R.M. Org. Lett. 5 (2003) 2095
23. Magnus P., Mattews K.S., and Lynch V. Org. Lett. 5 (2003) 2181
24. Stoltz B.M., Ashley E.R., and Cruz E.G. J. Am. Chem. Soc. 125 (2004) 15000
25. Kaufman T.S. Synthesis 3 (2005) 339
26. Magnus P., and Matthews K.S. J. Am. Chem. Soc. 127 (2005) 12476
27. Lane J.W., Chen Y., and Williams R.M. J. Am. Chem. Soc. 127 (2005) 12684
28. Kwon S., and Myers A.G. J. Am. Chem. Soc. 127 (2005) 16796
29. Wipf P., and Hopkins C.R. J. Org. Chem. 64 (1999) 6881
30. Wipf P., and Hopkins C.R. J. Org. Chem. 66 (2001) 3133
31. For reviews, see:
32. de Meijere A., and Meyer F.E. Angew. Chem., Int. Ed. Engl. 33 (1994) 2379
33. Gibson S.E., and Middleton R.J. Contemp. Org. Synth. 3 (1996) 447
34. Crisp G.T. Chem. Soc. Rev. 27 (1998) 427
35. Beletskaya I.P., and Cheprakov A.V. Chem. Rev. 100 (2000) 3009
36. Whitcombe N.J., Hii K.K., and Gibson S.E. Tetrahedron 57 (2001) 7449
37. Dounay A.B., and Overman L.E. Chem. Rev. 103 (2003) 2945
38. Farina V. Adv. Synth. Catal. 346 (2004) 1553
39. Nicolaou K.C., Bulger P.G., and Sarlah D.J. Angew. Chem., Int. Ed. 44 (2005) 4442
40. Alonso F., Beletskaya I.P., and Yus M. Tetrahedron 61 (2005) 11771
41. Grigg R., Sridharan V., Stevenson P., Sukirthalingam S., and Worakun T. Tetrahedron 46 (1990) 4003
42. Grigg R., Santhakumar V., Sridharan V., Stevenson P., Teasdale A., Thornton-Pett M., and Worakun T. Tetrahedron 47 (1991) 9703
43. Rawal V.H., Michoud C., and Monestel R. J. Am. Chem. Soc. 115 (1993) 3030
44. Kwon O., Su D.-S., Meng D., Deng W., D'Amico D.C., and Danishefsky S.J. Angew. Chem., Int. Ed. 37 (1998) 1877
45. Coe J.W. Org. Lett. 2 (2000) 4205
46. Endo A., Yanagisawa A., Abe M., Tohma S., Kan T., and Fukuyama T. J. Am. Chem. Soc. 124 (2002) 6552
47. Bashore C.G., Samardjiev I.J., Bordner J., and Coe J.W. J. Am. Chem. Soc. 125 (2003) 3268
48. Oliveira D.F., Miranda P.C.M.L., and Correia C.R.D. J. Org. Chem. 64 (1999) 6646
49. Coudert E., Acher F., and Azerad R. Synthesis (1997) 863
50. For the use of Pd-catalyzed coupling reactions of lactam-derived ketene aminal phosphates, see:
51. Nicolaou K.C., and Namoto S.K. Chem. Commun. (1998) 1757
52. Jiang J., DeVita R.J., Doss G.A., Goulet M.T., and Wyvratt M.J. J. Am. Chem. Soc. 121 (1999) 593
53. Lepifre F., Buon C., Rabot R., Bouyssou P., and Coudert G. Tetrahedron Lett. 40 (1999) 6373
54. Lepifre F., Clavier S., Bouyssou P., and Coudert G. Tetrahedron 57 (2001) 6969
55. Galbo F.L., Occhiato E., Guarna A., and Faggi C. J. Org. Chem. 68 (2003) 6360
56. For lactam-derived enol triflates in Pd-catalyzed coupling reactions, see:
57. Luker T., Hiemstra H., and Speckamp W.N. J. Org. Chem. 62 (1997) 8131
58. Papillon J.P.N., and Taylor R.J.K. Org. Lett. 2 (2000) 1987
59. Trost B.M., and Toste F.D. J. Am. Chem. Soc. 121 (1999) 4545
60. Trost B.M., and Lee C.B. J. Am. Chem. Soc. 123 (2001) 3671
61. Trost B.M. Chem. Pharm. Bull. 50 (2002) 1
62. Trost B.M., and Crawley M.L. Chem. Rev. 103 (2003) 2921
63. Trost B.M., Shen H.C., and Surivet J.-P. J. Am. Chem. Soc. 126 (2004) 12565
64. Trost B.M. J. Org. Chem. 69 (2004) 5813
65. Tsuji J. Proc. Jpn. Acad. 80 (2004) 349
66. See Ref. 7h.
67. Galland J.-C., Roland S., Malpart J., Savignac M., and Genet J.-P. Eur. J. Org. Chem. (1999) 621
68. Trost B.M., Sacchi K.L., Schroeder G.M., and Asakawa N. Org. Lett. 4 (2002) 3427
69. Seo S.-Y., Jung J.-K., Paek S.-M., Lee Y.-S., Kim S.-H., Lee K.-O., and Suh Y.-G. Org. Lett. 6 (2004) 429
70. Grigg R., Lansdell M.I., and Thornton-Pett M. Tetrahedron 55 (1999) 2025
71. Tsuji J. Palladium Reagents and Catalysts (1995), Wiley, New York, NY Chapter 4, p 125
72. Li H., Jiang X., Ye Y.-h., Fan C., Romoff T., and Goodman M. Org. Lett. 1 (1999) 91
73. Karoyan P., and Chassaing G. Tetrahedron Lett. 38 (1997) 85