Development of radical addition-cyclization-elimination reaction of oxime ether and its application to formal synthesis of (±)-martinelline

Tetrahedron

Volumn 63, Issue 40, 2007, Pages 10092-10117

  Miyata, Okiko ^a   Shirai, Atsushi ^a   Yoshino, Shintaro ^a   Nakabayashi, Toshiki ^a   Takeda, Yoshifumi ^a   Kiguchi, Toshiko ^a   Fukumoto, Daisuke ^a   Ueda, Masafumi ^a   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

, unsaturated ester; Martinelline; Oxime ether; Pyrroloquinoline; Radical reaction

Indexed keywords

ANTIMALARIAL AGENT; MARTINELLINE; QUINOLINE DERIVATIVE;

ADDITION REACTION; ANTIMALARIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS; ELIMINATION REACTION; INFRARED SPECTROSCOPY; MALARIA; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 34547933664     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.07.007     Document Type: Article

References (93)

1. In: Renaud P., and Sibi M.P. (Eds). Radicals in Organic Synthesis Vols. 1 and 2 (2001), Wiley-VCH, Weinheim
2. Tietze L.F., Brasche G., and Gericke K.M. In: Tietze L.F., Brasche G., and Gericke K.M. (Eds). Domino Reactions in Organic Synthesis (2006), Wiley-VCH, Weinheim 219-279
3. Naito T., Honda Y., Miyata O., and Ninomiya I. J. Chem. Soc., Perkin Trans. 1 (1995) 19-26
4. Miyata O., Nishiguchi A., Ninomiya I., Naito T., Aoe K., and Okamura K. Tetrahedron Lett. 37 (1996) 229-232
5. Miyata O., Nishiguchi A., Ninomiya I., Naito T., Aoe K., and Okamura K. Chem. Pharm. Bull. 44 (1996) 1285-1287
6. Naito T., Honda Y., Bhavakul V., Yamaguchi S., Fujiwara A., Miyata O., and Ninomiya I. Chem. Pharm. Bull. 45 (1997) 1932-1939
7. Miyata O., Nishiguchi A., Ninomiya I., Aoe K., Okamura K., and Naito T. J. Org. Chem. 65 (2000) 6922-6931
8. Miyata O., Ozawa Y., Ninomiya I., and Naito T. Tetrahedron 56 (2000) 6199-6207
9. Miyata O., Nakajima E., and Naito T. Chem. Pharm. Bull. 49 (2001) 213-224
10. Miyata O., and Naito T. C. R. Acad. Sci. Paris Chim. 4 (2001) 401-421
11. Miyata O., Muroya K., Kobayashi T., Yamanaka R., Kajisa S., Koide J., and Naito T. Tetrahedron 58 (2002) 4459-4479
12. Miyabe H., Fujii K., Goto T., and Naito T. Org. Lett. 2 (2000) 4071-4074
13. Miyabe H., Fujii K., Tanaka H., and Naito T. Chem. Commun. (2001) 831-832
14. Miyabe H., Tanaka H., and Naito T. Tetrahedron Lett. 40 (1999) 8387-8390
15. Miyabe H., Ueda M., Fujii K., Nishimura A., and Naito T. J. Org. Chem. 68 (2003) 5618-5626
16. Ueda M., Miyabe H., Nishimura A., Miyata O., and Naito T. Org. Lett. 5 (2003) 3835-3838
17. Miyabe H., Tanaka H., and Naito T. Chem. Pharm. Bull. 52 (2004) 842-847
18. Naito T., Nakagawa K., Nakamura T., Kasei A., Ninomiya I., and Kiguchi T. J. Org. Chem. 64 (1999) 2003-2009
19. Naito T., Tajiri K., Harimoto T., Ninomiya I., and Kiguchi T. Tetrahedron Lett. 35 (1994) 2205-2206
20. Miyabe H., Torieda M., Inoue K., Tajiri K., Kiguchi T., and Naito T. J. Org. Chem. 63 (1998) 4397-4407
21. Miyabe H., Torieda M., Ninomiya I., Kiguchi T., and Naito T. Synlett (1997) 580-582
22. Naito T., Torieda M., Tajiri K., Ninomiya I., and Kiguchi T. Chem. Pharm. Bull. 44 (1996) 624-626
23. Naito T., Fukumoto D., Takebayashi K., and Kiguchi T. Heterocycles 51 (1999) 489-492
24. Miyabe H., Kanehira S., Kume K., Kandori H., and Naito T. Tetrahedron 54 (1998) 5883-5892
25. Kiguchi T., Ozaki M., and Naito T. Heterocycles 51 (1999) 2711-2722
26. Kiguchi T., Tajiri K., Ninomiya I., and Naito T. Tetrahedron 56 (2000) 5819-5833
27. Naito T., Nair J.S., Nishiki A., Yamashita K., and Kiguchi T. Heterocycles 53 (2000) 2611-2615
28. Miyabe H., Tanaka H., and Naito T. Chem. Pharm. Bull. 52 (2004) 74-78
29. Miyabe H., Nishiki A., and Naito T. Chem. Pharm. Bull. 51 (2003) 100-103
30. Formal total synthesis of martinelline and martinellic acid, see:
31. Hadden M., Nieuwenhuyzen M., Potts D., Stevenson P.J., Thompson N., and Walker D.A. Tetrahedron 62 (2006) 3977-3984
32. He Y., Mahmud H., Moningka R., Lovely C.J., and Dias H.V.R. Tetrahedron 62 (2006) 8755-8769
33. Takeda Y., Nakabayashi T., Shirai A., Fukumoto D., Kiguchi T., and Naito T. Tetrahedron Lett. 45 (2004) 3481-3484
34. Miyata O., Shirai A., Yoshino S., Takeda Y., Sugiura M., and Naito T. Synlett (2006) 893-896
35. Hadden M., Nieuwenhuyzen M., Osborne D., Stevenson P.J., and Thompson N. Tetrahedron Lett. 42 (2001) 6417-6419
36. He Y., Moningka R., Mahmud H., and Lovely C.J. Tetrahedron Lett. 46 (2005) 1251-1254
37. Balasubramanian M., and Keay J.G. In: Katrizky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry Vol. 5 (1996), Pergamon, London 245-300 Chapter 5.06
38. Hewson A.T., Hughes K., Richardson S.K., Sharpe D.A., and Wadsworth A.H. J. Chem. Soc., Perkin Trans. 1 (1991) 1565-1569
39. Hechavarria Fonseca M., Eibler E., Zabel M., and Konig B. Tetrahedron: Asymmetry 14 (2003) 1989-1994
40. Bertrand M.P., Escoubet S., Gastaldi S., and Timokhin V.I. Chem. Commun. (2002) 216-217
41. Escoubet S., Gastaldi S., Timokhin V.I., Bertrand M.P., and Siri D. J. Am. Chem. Soc. 126 (2004) 12343-12352
42. Jones K., and Lappert M.F. J. Chem. Soc. (1965) 1944-1951
43. Dimopoulos P., Athlan A., Manaviazar S., George J., Walters M., Lazarides L., Aliev A.E., and Hale K.J. Org. Lett. 7 (2005) 5369-5372
44. Nativi C., and Taddei M. J. Org. Chem. 53 (1988) 820-826
45. Corsaro A., Chiacchio U., Caramella P., and Purrello G. J. Heterocycl. Chem. 21 (1984) 949-952
46. Witherup K.M., Ransom R.W., Graham A.C., Bernard A.M., Salvatore M.J., Lumma W.C., Anderson P.S., Pitzenberger S.M., and Varga S.L. J. Am. Chem. Soc. 117 (1995) 6682-6685
47. Total synthesis of martinelline and martinellic acid, see:
48. Snider B.B., Ahn Y., and O'Hare S.M. Org. Lett. 3 (2001) 4217-4220
49. Powell D.A., and Batey R.A. Org. Lett. 4 (2002) 2913-2916
50. Ma D., Xia C., Jiang J., and Zhang J. Org. Lett. 3 (2001) 2189-2191
51. Xia C., Heng L., and Ma D. Tetrahedron Lett. 43 (2002) 9405-9409
52. Ma D., Xia C., Jiang J., Zhang J., and Tang W. J. Org. Chem. 68 (2003) 442-451
53. Ikeda S., Shibuya M., and Iwabuchi Y. Chem. Commun. (2007) 504-506
54. Badarinarayana V., and Lovely C.J. Tetrahedron Lett. 48 (2007) 2607-2610
55. Synthesis of the pyrroloquinoline core, see:
56. Gurjar M.K., Pal S., and Rama Rao A.V. Heterocycles 45 (1997) 231-234
57. Ho T.C.T., and Jones K. Tetrahedron 53 (1997) 8287-8294
58. Batey R.A., Simoncic P.D., Lin D., Smyj R.P., and Lough A.J. Chem. Commun. (1999) 651-652
59. Hadden M., and Stevenson P.J. Tetrahedron Lett. 40 (1999) 1215-1218
60. Lovely C.J., and Mahmud H. Tetrahedron Lett. 40 (1999) 2079-2082
61. Snider B.B., Ahn Y., and Foxman B.M. Tetrahedron Lett. 40 (1999) 3339-3342
62. Frank K.E., and Aubé J. J. Org. Chem. 65 (2000) 655-666
63. Nieman J.A., and Ennis M.D. Org. Lett. 2 (2000) 1395-1397
64. Nyerges M., Fejes I., and Toke L. Tetrahedron Lett. 41 (2000) 7951-7954
65. Snider B.B., and O'Hare S.M. Tetrahedron Lett. 42 (2001) 2455-2458
66. Mahmud H., Lovely C.J., and Dias H.V.R. Tetrahedron 57 (2001) 4095-4105
67. Hadden M., Nieuwenhuyzen M., Potts D., Stevenson P.J., and Thompson N. Tetrahedron 57 (2001) 5615-5624
68. Batey R.A., and Powell D.A. Chem. Commun. (2001) 2362-2363
69. Hamada Y., Kunimune I., and Hara O. Heterocycles 56 (2002) 97-100
70. He Y., Mahmud H., Wayland B.R., Dias H.V.R., and Lovely C.J. Tetrahedron Lett. 43 (2002) 1171-1174
71. Malassene R., Sanchez-Bajo L., Toupet L., Hurvois J.-P., and Moinet C. Synlett (2002) 1500-1504
72. Nyerges M., Fejes I., and Toke L. Synthesis (2002) 1823-1828
73. Hara O., Sugimoto K., Makino K., and Hamada Y. Synlett (2004) 1625-1627
74. Hara O., Sugimoto K., Makino K., and Hamada Y. Tetrahedron 60 (2004) 9381-9390
75. Yadav J.S., Subba R.B.V., Sunitha V., Srinivasa R.K., and Ramakrishna K.V.S. Tetrahedron Lett. 45 (2004) 7947-7950
76. Nyerges M. Heterocycles 63 (2004) 1685-1712
77. Shaw J.T., Masse C.E., and Ng P.Y. Org. Lett. 8 (2006) 3999-4002
78. Astill B.D., and Boekelheide V. J. Am. Chem. Soc. 77 (1955) 4079-4084
79. Jiang Y., and Ma D. Tetrahedron Lett. 43 (2002) 7013-7015
80. Beaulieu F., Arora J., Veith U., Taylor N.J., Chapell B.J., and Snieckus V. J. Am. Chem. Soc. 118 (1996) 8727-8728
81. Williams L., Booth S.E., and Undheim K. Tetrahedron 50 (1994) 13697-13708
82. Nagarajan K., Nair M.D., and Pillai P.M. Tetrahedron 23 (1967) 1683-1690
83. Harayama T., Sato T., Hori A., Abe H., and Takeuchi Y. Heterocycles 66 (2005) 527-530
84. Crabb T.A., and Soilleux S.L. J. Chem. Soc., Perkin Trans. 1 (1985) 1381-1385
85. Kunz H., and Dombo B. Angew. Chem., Int. Ed. Engl. 27 (1988) 711-713
86. Elliott M., Farnham A.W., Janes N.F., Johnson D.M., and Pulman D.A. Pestic. Sci. 18 (1987) 229-238
87. Orsini F., Pelizzoni F., and Ricca G. Synth. Commun. 12 (1982) 1147-1154
88. Salamonczyk G.M., Han K., Guo Z., and Sih C.J. J. Org. Chem. 61 (1996) 6893-6900
89. Kirsop P., Storey J.M.D., and Harrison W.T.A. Acta Crystallogr. 9 (2004) 1636-1638
90. Sarrazin L., and Mauze B. Synth. Commun. (1996) 3179-3191
91. Bailey W.J., and Bello J. J. Org. Chem. 20 (1955) 525-529
92. Carril M., SanMartin R., Dominguez E., and Tellitu I. Tetrahedron 63 (2006) 690-702
93. Carril M., SanMartin R., Churruca F., Tellitu I., and Dominguez E. Org. Lett. 7 (2005) 4787-4789