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0012054405
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D. A. Evans, H. A. Rajapakse, D. Stenkamp, Angew. Chem. 2002, 114, 4751; Angew. Chem. Int. Ed. 2002, 41, 4569.
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Evans, D.A.1
Rajapakse, H.A.2
Stenkamp, D.3
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2
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0037011207
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D. A. Evans, H. A. Rajapakse, D. Stenkamp, Angew. Chem. 2002, 114, 4751; Angew. Chem. Int. Ed. 2002, 41, 4569.
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3
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85007652483
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note
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A full account of this work will be published in due course.
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6
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85007652485
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note
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2O = di-tert-butyl dicarbonate; LDA = lithium diisopropylamide; HMPA = hexamethylphosphoramide; TBODPS = tert-butoxydiphenylsilyl; RT= room temperature; TAS-F = tris(dimethyamino)sulfur(trimethylsilyl)difluoride.
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7
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0035847479
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A. Chen, A. Nelson, N. Tanikkul, E. J. Thomas, Tetrahedron Lett. 2001, 42, 1251-1254.
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Tetrahedron Lett.
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Chen, A.1
Nelson, A.2
Tanikkul, N.3
Thomas, E.J.4
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8
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33847085984
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S. H. Pine, R. Zahler, D. A. Evans, R. H. Grubbs, J. Am. Chem. Soc. 1980, 102, 3270.
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Pine, S.H.1
Zahler, R.2
Evans, D.A.3
Grubbs, R.H.4
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11
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0028937415
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32 benzyl ether to form the corresponding tetrahydrofuran was observed, For a similar side reaction, see: D. A. Evans, A. M. Ratz, B. E. Huff, G. S. Sheppard, J. Am. Chem. Soc. 1995, 117, 3448-3467.
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J. Am. Chem. Soc.
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Evans, D.A.1
Ratz, A.M.2
Huff, B.E.3
Sheppard, G.S.4
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12
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0030781007
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D. A. Evans, D. W. C. MacMillan, K. R. Campos, J. Am. Chem. Soc. 1997, 119, 10859-10860.
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Evans, D.A.1
MacMillan, D.W.C.2
Campos, K.R.3
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13
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0025073031
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T. Fukuyama, S.-L. Lin, L. Li, J. Am. Chem. Soc. 1990, 112, 7050-7051; see also; D. A. Evans, B. W. Trotter, P. J. Coleman, B. Cote, L. Carlos Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726.
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J. Am. Chem. Soc.
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Fukuyama, T.1
Lin, S.-L.2
Li, L.3
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14
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0033575415
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T. Fukuyama, S.-L. Lin, L. Li, J. Am. Chem. Soc. 1990, 112, 7050-7051; see also; D. A. Evans, B. W. Trotter, P. J. Coleman, B. Cote, L. Carlos Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726.
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Evans, D.A.1
Trotter, B.W.2
Coleman, P.J.3
Cote, B.4
Carlos Dias, L.5
Rajapakse, H.A.6
Tyler, A.N.7
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15
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0025354154
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Conditions adapted from: M. Hartman, E. Zibral, Tetrahedron Lett. 1990, 31, 2875-2878. Both Wittig and Petersen conditions resulted in aldehyde decomposition with no observed product.
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Tetrahedron Lett.
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Hartman, M.1
Zibral, E.2
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16
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0000441415
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D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc. 1992, 114, 6671-6674.
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Evans, D.A.1
Fu, G.C.2
Hoveyda, A.H.3
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17
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49249151283
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B. E. Rossiter, T. R. Verhoeven, K. B. Sharpless, Tetrahedron Lett. 1979, 20, 4733-4736.
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Rossiter, B.E.1
Verhoeven, T.R.2
Sharpless, K.B.3
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20
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85007647941
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note
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No undesired tetrahydropyran byproducts were observed in this reaction.
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21
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0000355152
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J. B. Baudin, G. Hareau, S. A. Julia, O. Ruel, Bull. Soc. Chim. Fr. 1993, 130, 856-878.
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Baudin, J.B.1
Hareau, G.2
Julia, S.A.3
Ruel, O.4
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22
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0032537206
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PMB deprotection with DDQ was incompatible with the pectenotoxin diene, as exclusive allylic oxidation was observed. For successful deprotections of PMB ethers in the presence of allylic dienes see: a) N. Murakami, W. Wang, M. Aoki, Y. Tsutsui, M. Sugimoto, M. Kobayashi, Tetrahedron Lett. 1998, 39, 2349-2352;
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Tetrahedron Lett.
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Murakami, N.1
Wang, W.2
Aoki, M.3
Tsutsui, Y.4
Sugimoto, M.5
Kobayashi, M.6
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23
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0032514515
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b) G. Pattenden, A. T. Plowright, J. T. Tornos, T. Ye, Tetrahedron Lett. 1998, 39, 6099-6102.
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(1998)
Tetrahedron Lett.
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Pattenden, G.1
Plowright, A.T.2
Tornos, J.T.3
Ye, T.4
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25
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0026005895
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b) D. A. Evans, R. P. Polniaszek, K. M. DeVries, D. E. Guinn, D. J. Mathre, J. Am. Chem. Soc. 1991, 113, 7613-7630.
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Evans, D.A.1
Polniaszek, R.P.2
DeVries, K.M.3
Guinn, D.E.4
Mathre, D.J.5
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26
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85007646907
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ref. [19b]
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a) ref. [19b];
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27
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0034684178
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b) D. A. Evans, D. M. Fitch, T. E. Smith, V. J. Cee, J. Am. Chem. Soc. 2000, 122, 10033-10046; A. B. Smith, B. M. Brandt, Org. Lett. 2001, 3, 1685-1688.
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Evans, D.A.1
Fitch, D.M.2
Smith, T.E.3
Cee, V.J.4
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28
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0035979030
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b) D. A. Evans, D. M. Fitch, T. E. Smith, V. J. Cee, J. Am. Chem. Soc. 2000, 122, 10033-10046; A. B. Smith, B. M. Brandt, Org. Lett. 2001, 3, 1685-1688.
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Org. Lett.
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Smith, A.B.1
Brandt, B.M.2
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30
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85007646205
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note
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Initial feasibility studies on a model system revealed a dramatic counterion effect for this Julia coupling reaction. The use of KHMDS as the base resulted in a 29:71 ratio of C32 epimers favoring the undesired product. We attribute this epimerization side reaction to be due to ring-F cleavage through β-alkoxy elimination and readdition to the intermediate unsaturated sulfone.
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31
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0030912448
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D. A. Evans, P. H. Carter, C. J. Dinsmore, J. C. Barrow, J. L. Katz, D. W. Kung, Tetrahedron Lett. 1997, 38, 4535-4538.
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Tetrahedron Lett.
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Evans, D.A.1
Carter, P.H.2
Dinsmore, C.J.3
Barrow, J.C.4
Katz, J.L.5
Kung, D.W.6
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32
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0001616071
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J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
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Inanaga, J.1
Hirata, K.2
Saeki, H.3
Katsuki, T.4
Yamaguchi, M.5
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33
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0001409192
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K. A. Scheidt, H. Chen, B. C. Follows, S. R. Chemler, D. S. Coffey, W. R. Roush, J. Org. Chem. 1998, 63, 6436-6437.
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Scheidt, K.A.1
Chen, H.2
Follows, B.C.3
Chemler, S.R.4
Coffey, D.S.5
Roush, W.R.6
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34
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0028213668
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a) For previous uses of TAS-F for silyl ether deprotection see: 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. 1994, 116, 1597-1598;
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Holton, R.A.1
Somoza, C.2
Kim, H.-B.3
Liang, F.4
Biediger, R.J.5
Boatman, P.D.6
Shindo, M.7
Smith, C.C.8
Kim, S.9
Nadizadeh, H.10
Suzuki, Y.11
Tao, C.12
Vu, P.13
Tang, S.14
Zhang, P.15
Murthi, K.K.16
Gentile, L.N.17
Liu, J.H.18
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35
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0030889501
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b) P. A. Wender, N. F. Badham, S. P. Conway, P. E. Floreancig, T. E. Glass, C. Grånicher, J. B. Houze, J. Jånichen, D. Lee, D. G. Marquess, P. L. McGrane, W. Meng, T. P. Mucciaro, M. Muhnlebach, M. G. Natchus, H. Paulsen, D. B. Rawlings, J. Satkofsky, A. J. Shuker, J. C. Sutton, R. E. Taylor, K. Tomooka, J. Am. Chem. Soc. 1997, 119, 2755-2756.
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Wender, P.A.1
Badham, N.F.2
Conway, S.P.3
Floreancig, P.E.4
Glass, T.E.5
Grånicher, C.6
Houze, J.B.7
Jånichen, J.8
Lee, D.9
Marquess, D.G.10
McGrane, P.L.11
Meng, W.12
Mucciaro, T.P.13
Muhnlebach, M.14
Natchus, M.G.15
Paulsen, H.16
Rawlings, D.B.17
Satkofsky, J.18
Shuker, A.J.19
Sutton, J.C.20
Taylor, R.E.21
Tomooka, K.22
more..
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36
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85007633317
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note
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1H NMR spectra of pectenotoxin-1, -4, and -8, as well as samples of pectenotoxin-1 and -8.
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37
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0032540486
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K. Sasaki, J. L. C. Wright, T. Yasumoto, J. Org. Chem. 1998, 63, 2475-2480. We observed a 11:10:79 ratio of pectenotoxins-1:-4:-8.
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Sasaki, K.1
Wright, J.L.C.2
Yasumoto, T.3
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