5442
S. Schiltz et al. / Journal of Organometallic Chemistry 691 (2006) 5438–5443
O
O
O
O
5 mol%
Grubbs 2
CH2Cl2
reflux
30 min
O
O
22a
O
O
O
O
87%
26
27
E/Z = 3:1 26/27 = 3:1 E/Z = 3:1
5 mol% Grubbs 2
1,2-Dichloroethane
80°C, 5 min
O
O
O
O
quant.
22b
28b
Scheme 9.
(f) K.C. Nicolaou, Z. Yang, J.J. Liu, P.G. Nantermet, C.F.
Claiborne, J. Renaud, R.K. Guy, K. Shibayama, J. Am. Chem.
Soc. 117 (1995) 645;
(g) K.C. Nicolaou, H. Ueno, J.J. Liu, P.G. Nantermet, Z. Yang, J.
Renaud, K. Paulvannan, R. Chadha, J. Am. Chem. Soc. 117 (1995)
653;
O
O
O
O
O
O
O
O
29a
29b
30a
30b
5 mol% [RuIMes]
(h) R.A. Holton, C. Somoza, H.B. Kim, F. Liang, R.J. Biediger,
P.D. Boatman, M. Shindo, C.C. Smith, S. Kim, H. Nadizadeh, Y.
Suzuki, C. Tao, P. Vu, S. Tang, P. Zhang, K.K. Murthi, L.N.
Gentile, J.H. Liu, J. Am. Chem. Soc. 116 (1994) 1597;
(i) R.A. Holton, H.B. Kim, C. Somoza, F. Liang, R.J. Biediger, P.D.
Boatman, M. Shindo, C.C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki,
C. Tao, P. Vu, S. Tang, P. Zhang, K.K. Murthi, L.N. Gentile, J.H.
Liu, J. Am. Chem. Soc. 116 (1994) 1599;
1,2-Dichloroethane
reflux
12 h
(j) J.J. Masters, J.T. Link, L.B. Snyder, W.B. Young, S. Danishefsky,
Angew. Chem., Int. Ed. Engl. 34 (1995) 1723;
Scheme 10.
(k) P.A. Wender, N.F. Badham, S.P. Conway, P.E. Floreancig, T.E.
Glass, C. Gra¨nicher, J.B. Houze, J. Ja¨nichen, D. Lee, D.G. Marquess,
P.L. McGrane, W. Meng, T.P. Mucciaro, M. Mu¨hlebach, M.G.
Natchus, H. Paulsen, D.B. Rawlins, J. Satkofsky, A.J. Shuker, J.C.
Sutton, R.E. Taylor, K. Tomooka, J. Am. Chem. Soc. 119 (1997) 2755;
(l) P.A. Wender, N.F. Badham, S.P. Conway, P.E. Floreancig, T.E.
Glass, J.B. Houze, N.E. Krauss, D. Lee, D.G. Marquess, P.L.
McGrane, W. Meng, M.G. Natchus, A.J. Shuker, J.C. Sutton, R.E.
Taylor, J. Am. Chem. Soc. 119 (1997) 2757;
Acknowledgements
Financial support was provided by the CNRS and the
´ ´
Ecole Polytechnique. S.S. acknowledges the Delegation
´ ´
Generale pour l’Armement (DGA) for a fellowship. We
thank Dr. Ange Pancrazi for helpful discussion.
(m) T. Mukaiyama, I. Shiina, H. Iwadare, M. Saitoh, T. Nishimura,
N. Ohkawa, H. Sakoh, H. Nishimura, Y.-I. Tani, M. Hasegawa, K.
Yamada, K. Saito, Chem. Eur. J. 5 (1999) 121;
References
(n) K. Morihara, R. Hara, S. Kawahara, T. Nishimori, N. Nakamura,
H. Kusama, I. Kuwajima, J. Am. Chem. Soc. 120 (1998) 12980.
[3] C.S. Swindell, B.P. Patel, J. Org. Chem. 55 (1990) 3.
[4] For previous work from this laboratory on syntheses of model BC
ring-systems of taxol involving RCM between C9 and C10, see: (a) D.
Bourgeois, A. Pancrazi, L. Ricard, J. Prunet, Angew. Chem., Int. Ed.
Engl. 39 (2000) 725;
[1] N.H. Oberlies, D.J. Kroll, J. Nat. Prod. 67 (2004) 129.
[2] For reviews on the chemistry of taxol, see: (a) K.C. Nicolaou, W.-M.
Dai, R.K. Guy, Angew. Chem., Int. Ed. Engl. 33 (1994) 15;
(b) D.G.I. Kingston, Chem. Commun. (2001) 867;
For the total syntheses, see: (c) K.C. Nicolaou, Z. Yang, J.J. Liu, H.
Ueno, P.G. Nantermet, R.K. Guy, C.F. Claiborne, J. Renaud, E.A.
Couladouros, K. Paulvannan, E.J. Sorensen, Nature 367 (1994) 630;
(d) K.C. Nicolaou, P.G. Nantermet, H. Ueno, R.K. Guy, E.A.
Couladouros, E.J. Sorensen, J. Am. Chem. Soc. 117 (1995) 624;
(e) K.C. Nicolaou, J.J. Liu, Z. Yang, H. Ueno, E.J. Sorensen, C.F.
Claiborne, R.K. Guy, C.K. Hwang, M. Nakada, P.G. Nantermet, J.
Am. Chem. Soc. 117 (1995) 634;
(b) D. Bourgeois, J. Mahuteau, A. Pancrazi, S.P. Nolan, J. Prunet,
Synthesis (2000) 869.
´
[5] C. Petrier, J.-L. Luche, J. Org. Chem. 50 (1985) 12.
[6] M. Frigerio, M. Santagostino, S. Sputore, J. Org. Chem. 64 (1999)
4537.
[7] For a similar homologation, see Ref [4b] and: B. Muller, F. Delaloge,
´ ´
M. den Hartog, J.-P. Ferezou, A. Pancrazi, J. Prunet, J.-Y.