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A. Fürstner, G. Seidel, N. Kindler, Tetrahedron 1999, 55, 8215-8230;
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Fürstner, A.1
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Fürstner, A.1
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15
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0002437895
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For an authoritative and comprehensive review on epothilone syntheses by RCM see: K. C. Nicolaou, N. P. King, Y. He, Top. Organomet. Chem. 1998, 1, 73-104.
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a) R. R. Schrock, D. N. Clark, J. Sancho, J. H. Wengrovius, S. M. Rocklage, S. F. Pedersen, Organometallics 1982, 1, 1645-1651;
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b) J. H. Freudenberger, R. R. Schrock, M. R. Churchill, A. L. Rheingold, J. W. Ziller, Organometallics 1984, 3, 1563-1573;
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Freudenberger, J.H.1
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A. Fürstner, C. Mathes, C. W. Lehmann, J. Am. Chem. Soc. 1999, 121, 9453-9454.
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a) C. Cimino, A. Crispino, V. Di Marzo, G. Sodano, A. Spinella, G. Villani, Experientia 1991, 47, 56-60;
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b) G. Cimino, A. Spinella, G. Sodano, Tetrahedron Lett. 1989, 30, 3589-3592;
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29
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0016843151
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Compound 1 and other prostaglandin lactones have previously been prepared by conventional macrolactonization of the parent prostaglandins, see: a) E. J. Corey, K. C. Nicolaou, L. S. Melvin, J. Am. Chem. Soc. 1975, 97, 653-654;
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Corey, E.J.1
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31
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0020552045
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c) G. C. Bundy, D. C. Peterson, J. C. Cornette, W. L. Miller, C. H. Spilman, J. W. Wilks, J. Med. Chem. 1983,26,1089-1099;
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Spilman, C.H.5
Wilks, J.W.6
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32
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0020623134
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d) G. D. Bundy, D. R. Morton, D. C. Peterson, E. E. Nishizawa, W. L. Miller, J. Med. Chem. 1983, 26, 790-799.
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Bundy, G.D.1
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Miller, W.L.5
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35
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0000915015
-
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For reviews on "three-component coupling" see: a) R. Noyori, M. Suzuki, Angew. Chem. 1984, 96, 854-882;
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Noyori, R.1
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38
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0018134898
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S-M. L. Chen, R. E. Schaub, C. V. Grundziskas, J. Org. Chem. 1978, 43, 3450-3454.
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Chen, S.-M.L.1
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Grundziskas, C.V.3
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39
-
-
0023710574
-
-
13C NMR data. Careful analysis of the crude product by HPLC, however, shows that the purity is only about 90%. This material can be used directly in the next step, because the isomeric by-products do not undergo productive 1,4-addition, see: C. R. Johnson, T. D. Penning. J. Am. Chem. Soc. 1988, 110, 4726-4735.
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Johnson, C.R.1
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40
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0021510134
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a) For the preparation of enone 7 see: R. Noyori, I. Tomino, M. Yamada, M. Nishizawa, J. Am. Chem. Soc. 1984, 106, 6717-6725;
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Noyori, R.1
Tomino, I.2
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42
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68949147023
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2, and imidazole according to a literature procedure: G. L. Lange, C. Gottardo, Synth. Commun. 1990, 20, 1473-1479;
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Lange, G.L.1
Gottardo, C.2
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44
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0024987706
-
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The three-component coupling was essentially carried out as described in: M. Suzuki, Y. Morita, H. Koyano, M. Koga, R. Noyori, Tetrahedron 1990, 46, 4809-4822.
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Tetrahedron
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Suzuki, M.1
Morita, Y.2
Koyano, H.3
Koga, M.4
Noyori, R.5
-
45
-
-
85003669276
-
-
Determined by HPLC on a Chiracel OD-H column with n-heptane/2-propanol as mobile phase
-
a) Determined by HPLC on a Chiracel OD-H column with n-heptane/2-propanol as mobile phase.
-
-
-
-
46
-
-
85003430519
-
-
Determined by HPLC on a Chiralpak AD column with n-heptane/2-propanol (95:5) as mobile phase
-
b) Determined by HPLC on a Chiralpak AD column with n-heptane/2-propanol (95:5) as mobile phase.
-
-
-
-
47
-
-
85003430261
-
-
note
-
+], 1), 431 (1), 389 (33), 317 (18), 297 (8), 225 (5), 155 (5), 129 (10), 91(12), 75 (100)
-
-
-
-
48
-
-
85003509098
-
-
4Si (446.71): C 69.91, H 9.48; found: C 70.08, H 9.42
-
4Si (446.71): C 69.91, H 9.48; found: C 70.08, H 9.42.
-
-
-
-
49
-
-
37049112047
-
-
R. F. Newton, D. P. Reynolds, C. F. Webb, S. M. Roberts, J. Chem. Soc. Perkin Trans. 1 1981, 2055-2058.
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J. Chem. Soc. Perkin Trans. 1
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-
Newton, R.F.1
Reynolds, D.P.2
Webb, C.F.3
Roberts, S.M.4
-
50
-
-
0038542691
-
-
We consider the "economy of steps" as a strategic goal for target oriented syntheses in general, see: A. Fürstner, Synlett 1999, 1523-1533.
-
(1999)
Synlett
, pp. 1523-1533
-
-
Fürstner, A.1
-
51
-
-
85003548950
-
-
note
-
+], 24), 316 (38), 298 (13), 262 (39), 208 (63), 163 (64), 151 (22), 145 (15),133 (25), 121 (28), 107 (42), 91 (78), 79 (100), 67 (83), 55 (93).
-
-
-
-
52
-
-
0032478678
-
-
For a study on the solid phase synthesis of prostaglandin derivatives and of small prostaglandin libraries see: a) L. A. Thompson, F. L. Moore, Y. C. Moon, J. A. Ellman, J. Org. Chem. 1998, 63, 2066-2067;
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(1998)
J. Org. Chem.
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Thompson, L.A.1
Moore, F.L.2
Moon, Y.C.3
Ellman, J.A.4
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53
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0033223066
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b) D. R. Dragoli, L. A. Thompson, J. O'Brien, J. A. Ellman, J. Comb. Chem. 1999, 1, 534-539;
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J. Comb. Chem.
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Dragoli, D.R.1
Thompson, L.A.2
O'Brien, J.3
Ellman, J.A.4
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54
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0033518061
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K. J. Lee, A. Angulo, P. Ghazal, K. D. Janda, Org. Lett. 1999, 1, 1859-1862.
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Org. Lett.
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Lee, K.J.1
Angulo, A.2
Ghazal, P.3
Janda, K.D.4
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