Tandem In-Mediated Carbometallation and Pd-Catalyzed Cross-Coupling
FULL PAPERS
Theresidue was purified by column chromatography [silica gel,
hexane/AcOEt (5/1)] to give (Z)-13a; yield: 32.8 mg (90%, E/
Z¼4/96).
2588–2603; c) L. Sun, N. Tran, C. Liang, S. Hubbard, F.
Tang, K. Lipson, R. Schreck, Y. Zhou, G. McMahon, C.
Tang, J. Med. Chem. 2000, 43, 2655–2663; d) M. Vieth,
D. J. Cummins, J. Med. Chem. 2000, 43, 3020–3032;
e) H. N. Bramson, J. Corona, S. T. Davis, S. H. Dicker-
son, M. Edelstein, S. V. Frye, R. T. Gampe Jr., P. A. Har-
ris, A. Hassell, W. D. Holmes, R. N. Hunter, K. E. Lack-
ey, B. Lovejoy, M. J. Luzzio, V. Montana, W. J. Rocque,
D. Rusnak, L. Schewchuk, J. M. Veal, D. H. Walker,
L. F. Kuyper, J. Med. Chem. 2001, 44, 4339–4358; f) L.
Sun, C. Liang, S. Shirazian, Y. Zhou, T. Miller, J. Cui,
J. Y. Fukuda, J.-Y. Chu, A. Nematalla, X. Wang, H.
Chen, A. Sistla, T. C. Luu, F. Tang, J. Wei, C. Tang, J.
Med. Chem. 2003, 46, 1116–1119.
Acknowledgements
This work was supported in part by Grant-in-Aid for Scientific
Research (B) and (C) from the Ministry of Education, Science,
Sports, and Culture, Japan, and by the 21st Century COE Pro-
gram “Knowledge Information Infrastructure for Genome Sci-
ence”.
References and Notes
[7] C. L. Woodard, Z. Li, A. K. Kathcart, J. Terrell, L. Ger-
ena, M. L. Sanchez, D. E. Kyle, A. K. Bhattacharjee,
D. A. Nichols, W. Ellis, S. T. Prigge, J. A. Geyer, N. C.
Waters, J. Med. Chem. 2003, 46, 3877–3882.
[8] R. P. Robinson, L. A. Reiter, W. E. Barth, A. M. Campe-
ta, K. Cooper, B. J. Cronin, R. Destito, K. M. Donahue,
F. C. Falkner, E. F. Fiese, D. L. Johnson, A. V. Kuper-
man, T. E. Liston, D. Malloy, J. J. Martin, D. Y. Mitchell,
F. W. Rusek, S. L. Shamblin, C. F. Wright, J. Med. Chem.
1996, 39, 10–18.
[1] For example, olefin metathesis: a) S. B. Garber, J. S.
Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem.
Soc, 2000, 122, 8168–879; b) L. Anastasia, Y. R. Du-
mond, E. Negishi, Eur. J. Org. Chem. 2001, 3039–3043;
c) Q. Yao, Y. Zhang, J. Am. Chem. Soc, 2004, 126, 74–
75; d) T. R. Hoye, C. S. Jeffrey, M. A. Tennakoon, J.
Wang, H. Zhao, J. Am. Chem. Soc, 2004, 126, 10210–
10211.
[2] For example, vinylic metal intermediates: a) M. Hojo, Y.
Murakami, H. Aihara, R. Sakuragi, Y. Baba, A. Hosomi,
Angew. Chem. Int. Ed. 2001, 40, 621–623; b) P. E. Tessi-
er, A. J. Penwell, F. E. S. Souza, A. G. Fallis, Org. Lett.
2003, 5, 2989–2992; c) S. J. Patel, T. F. Jamison, Angew.
Chem. Int. Ed. 2003, 42, 1364–1367; d) S. Ma, N. Jiao,
L. Ye, Chem. Eur. J. 2003, 9, 6049–6056; e) N. Zhu,
D. G. Hall, J. Org. Chem. 2003, 68, 6066–6069.
[3] a) T.-S. Kam, Y.-M. Choo, Tetrahedron 2000, 56, 6143–
6150; b) A. Cane, M.-C. Tournaire, D. Barritault, M. Cru-
meyrolle-Arias, Biochem. Biophys. Res. Commun. 2000,
276, 379–384; c) M. Tsuda, T. Mugishima, K. Komatsu,
T. Sone, M. Tanaka, Y. Mikami, M. Shiro, M. Hirai, Y.
Ohizumi, J. Kobayashi, Tetrahedron 2003, 59, 3227–
3230; d) C. Marti, E. M. Carreira, Eur. J. Org. Chem.
2003, 2209–2219; e) S. Akai, T. Tsujino, E. Akiyama,
K. Tanimoto, T. Naka, Y. Kita, J. Org. Chem. 2004, 69,
2478–2486.
[9] E:Z¼5:1–1:5, for example, a) M. Mori, Y. Ban, Tetra-
hedron Lett. 1979, 20, 1133–1136; b) M. R. Fielding, R.
Grigg, C. J. Urch, Chem. Commun. 2000, 2239–2240;
c) A. Teichert, K. Jantos, K. Harms, A. Studer, Org.
Lett. 2004, 6, 3477–3480.
[10] R. Yanada, S. Obika, M. Oyama, Y. Takemoto, Org. Lett.
2004, 6, 2825–2828.
[11] a) R. Yanada, N. Nishimori, A. Matsumura, N. Fujii, Y.
Takemoto, Tetrahedron Lett. 2002, 43, 4585–4588;
b) M. Ueda, H. Miyabe, A. Nishimura, O. Miyata, Y.
Takemoto, T. Naito, Org. Lett. 2003, 5, 3835–3838;
c) R. Yanada, Y. Koh, N. Nishimori, A. Matsumura, S.
Obika, H. Mitsuya, N. Fujii, Y. Takemoto, J. Org.
Chem. 2004, 69, 2417–2422; d) R. Yanada, S. Obika, N.
Nishimori, M. Yamauchi, Y. Takemoto, Tetrahedron
Lett. 2004, 45, 2331–2334.
[12] H. Miyabe, M. Ueda, A. Nishimura, T. Naito, Org. Lett.
2002, 4, 131–134.
[4] T. Y. Zhang, H. Zhang, Tetrahedron Lett. 2002, 43, 193–
195 and references cited therein.
[13] a) K. Inoue, A. Sawada, I. Shibata, A. Baba, J. Am.
Chem. Soc. 2002, 124, 906–907; b) B. C. Ranu, S. Saman-
ta, Tetrahedron 2003, 59, 7901–7904; c) B. C. Ranu, S.
Samanta, J. Org. Chem. 2003, 68, 7130–7132; d) B. C.
Ranu, S. Banerjee, A. Das, Tetrahedron Lett. 2004, 45,
8579–8581; e) C.-Y. Wang, H. Su, D.-Y. Yang, Synlett
2004, 561–563.
[14] a) S. A. Brunton, K. Jones, J. Chem. Soc. Perkin Trans. 1.
2000, 763–768; b) H. Ishibashi, T. Kobayashi, S. Nakashi-
ma, O. Tamura, J. Org. Chem. 2000, 65, 9022–9027; c) J.-
P. Bouvier, G. Jung, Z. Liu, B. Guerin, Y. Guindon, Org.
Lett. 2001, 3, 1391–1394; d) T. Ooi, M. Furuya, D. Sakai,
Y. Hokke, K. Maruoka, Synlett 2001, 541–543; e) H. Yor-
imitsu, K. Oshima, Bull. Chem. Soc. Jpn. 2002, 75, 853–
854.
[5] a) D. Ma, Q. Wu, Tetrahedron Lett. 2000, 41, 9089–9093;
b) S. Lin, S. J. Danishefsky, Angew. Chem. Int. Ed. 2001,
40, 1967–1970; c) M. Inoue, H. Furuyama, H. Sakazaki,
M. Hirama, Org. Lett. 2001, 3, 2863–2865; d) S. Lin,
S. J. Danishefsky, Angew. Chem. Int. Ed. 2002, 41, 512–
515; e) M. Kaiser, M. Groll, C. Renner, R. Huber, L. Mo-
roder, Angew. Chem. Int. Ed. 2002, 41, 780–783; f) B. K.
Albrecht, R. M. Williams, Org. Lett. 2003, 5, 197–200;
g) S. Lin, Z.-Q. Yang, B. H. B. Kwok, M. Koldobskiy,
C. M. Crews, S. J. Danishefsky, J. Am. Chem. Soc. 2004,
126, 6347–6355.
[6] a) M. Mohammadi, G. McMahon, L. Sun, C. Tang, P.
Hirth, B. K. Yeh, S. R. Hubbard, J. Schlessinger, Science
1997, 276, 955–960; b) L. Sun, N. Tran, F. Tang, H. App,
P. Hirth, G. McMahon, C. Tang, J. Med. Chem. 1998, 41,
[15] a) L. A. Paquette, T. M. Mitzel, J. Am. Chem. Soc. 1996,
118, 1931–1937; b) L. A. Paquette, G. D. Bennett, M. B.
Adv. Synth. Catal. 2005, 347, 1632 – 1642
ꢀ 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
1641