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(a) Kim, C.-G.; Kirschning, A.; Bergon, P.; Zhou, P.; Su, E.; Sauerbrei, B.; Ning, S.; Ahn, Y.; Breuer, M.; Leistner, E.; Floss, H. G. J. Am. Chem. Soc. 1996, 118, 7486.
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Lewis, N.6
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23
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0029925759
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For other syntheses of manumycin-type natural products, see: (a) Kapfer, I.; Lewis, N. J.; Macdonald, G.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 2101. (b) Alcaraz, L.; Macdonald, G.; Kapfer, I.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 6619. (c) Macdonald, G.; Lewis, N. J.; Taylor, R. J. K. Chem. Commun. 1996, 2647. (d) Alcaraz, L.; Taylor, R. J. K. Chem. Commun. 1998, 1157.
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Taylor, R.J.K.4
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24
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0030565606
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For other syntheses of manumycin-type natural products, see: (a) Kapfer, I.; Lewis, N. J.; Macdonald, G.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 2101. (b) Alcaraz, L.; Macdonald, G.; Kapfer, I.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 6619. (c) Macdonald, G.; Lewis, N. J.; Taylor, R. J. K. Chem. Commun. 1996, 2647. (d) Alcaraz, L.; Taylor, R. J. K. Chem. Commun. 1998, 1157.
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Alcaraz, L.1
Macdonald, G.2
Kapfer, I.3
Lewis, N.J.4
Taylor, R.J.K.5
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25
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0029850984
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For other syntheses of manumycin-type natural products, see: (a) Kapfer, I.; Lewis, N. J.; Macdonald, G.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 2101. (b) Alcaraz, L.; Macdonald, G.; Kapfer, I.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 6619. (c) Macdonald, G.; Lewis, N. J.; Taylor, R. J. K. Chem. Commun. 1996, 2647. (d) Alcaraz, L.; Taylor, R. J. K. Chem. Commun. 1998, 1157.
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Chem. Commun.
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Macdonald, G.1
Lewis, N.J.2
Taylor, R.J.K.3
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26
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0032554776
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For other syntheses of manumycin-type natural products, see: (a) Kapfer, I.; Lewis, N. J.; Macdonald, G.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 2101. (b) Alcaraz, L.; Macdonald, G.; Kapfer, I.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 6619. (c) Macdonald, G.; Lewis, N. J.; Taylor, R. J. K. Chem. Commun. 1996, 2647. (d) Alcaraz, L.; Taylor, R. J. K. Chem. Commun. 1998, 1157.
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Chem. Commun.
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Alcaraz, L.1
Taylor, R.J.K.2
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27
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0001260043
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In preliminary communications, we have reported the preparation of polyene side chains of manumycins using organozirconocene methodology: (a) Wipf, P.; Xu, W.; Takahashi, H.; Jahn, H.; Coish, P. D. G. Pure Appl. Chem. 1997, 69, 639. (b) Wipf, P.; Coish, P. D. G. Tetrahedron Lett. 1997, 38, 5073.
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Wipf, P.1
Xu, W.2
Takahashi, H.3
Jahn, H.4
Coish, P.D.G.5
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28
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0030745359
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In preliminary communications, we have reported the preparation of polyene side chains of manumycins using organozirconocene methodology: (a) Wipf, P.; Xu, W.; Takahashi, H.; Jahn, H.; Coish, P. D. G. Pure Appl. Chem. 1997, 69, 639. (b) Wipf, P.; Coish, P. D. G. Tetrahedron Lett. 1997, 38, 5073.
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Tetrahedron Lett.
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Wipf, P.1
Coish, P.D.G.2
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35
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0345729480
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note
-
3) of an impure sample supported this assumption. Peak listings characteristic for the diketal: δ 3.13 (s, 6 H), 3.26 (s, 6 H), 4.54 (d, 2 H, J = 4.5 Hz), 5.19 (d, 1 H, J = 10.5 Hz), 5.23 (d, 1 H, J = 18 Hz), 5.75 (d, 1 H, J = 10.5 Hz), 5.8-6.0 (m, 1 H), 6.25 (dd, 1 H, J = 2.5, 10 Hz), 6.62 (br s, 1 H), 6.74 (br s, 1 H).
-
-
-
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36
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0345729483
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note
-
Other epoxidation protocols, including enantioselective procedures, were inefficient.
-
-
-
-
40
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0033534602
-
-
1H NMR δ 1.00-1.45 (m, 21 H), 5.99 (d, 1 H, J = 15.0 Hz), 6.01 (dd, 1 H, J = 10.5, 15.0 Hz), 6.33 (dd, 1 H, J = 10.5, 14.5 Hz), 6.43 (dd, 1 H, J = 10.5, 15.0 Hz), 6.52-6.75 (m, 4 H), 6.84 (dd, 1 H, J = 7.5, 10.0 Hz), 7.10-7.48 (m, 3 H)). For a related cis-trans isomerization during tin-iodine exchange, see: Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1989, 64, 23.
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J. Org. Chem.
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, pp. 23
-
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Mapp, A.K.1
Heathcock, C.H.2
-
41
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0344434876
-
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note
-
3-OD) δ 5.96 (d, 1 H, J = 15.0 Hz), 6.00 (d, 1 H, J = 13.0 Hz), 6.41 (dd, 1 H, J = 11.0, 15.0 Hz), 6.54 (dd, 1 H, J = 11.0, 15.0 Hz), 6.62-6.96 (m, 5 H), 7.12-7.40 (m, 3 H)).
-
-
-
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44
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0345297915
-
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note
-
Treatment of the vinylstannane with NBS at low temperature resulted in partial conversion to the vinyl bromide. For example, stirring the stannane with 1 equiv of NBS at -40 °C for 1 h gave a 44% yield of the vinyl bromide 24 and a 34% yield of recovered starting material. However, conducting the experiment at higher temperature (0 °C) resulted in complete consumption of stannane. At this temperature, the vinyl bromide was obtained in 82% yield as a single stereoisomer (see Experimental Section).
-
-
-
-
45
-
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0345297916
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note
-
This compound was prepared in 51% yield by Horner-Emmons condensation of β-tributylstannyl acrolein with N-methoxy-N-methyl-2-(triphenylphosphoranylidene)acetamide (see the Experimental Section).
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47
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0345297917
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note
-
This compound was prepared by Horner-Emmons condensation of β-tributylstannylacrolein with diethy(trimethylsilyloxycarbonyl-methy)phosphorane, followed by aqueous base workup and reprotection of the acid function using TIPS-Cl and imidazole (see the Experimental Section).
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48
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33847088408
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Negishi, E.-I.; King, A. O.; Okukado, N. J. Org. Chem. 1977, 42, 1821.
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Negishi, E.-I.1
King, A.O.2
Okukado, N.3
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50
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0001209154
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Buchwald, S. I.; LaMarie, S. J.; Nielson, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895.
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Buchwald, S.I.1
LaMarie, S.J.2
Nielson, R.B.3
Watson, B.T.4
King, S.M.5
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55
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0027997412
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Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
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(1994)
Synthesis
, pp. 639
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Ley, S.V.1
Norman, J.2
Griffith, W.P.3
Marsden, S.P.4
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