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For previous studies on bioactive marine lipids from our laboratory, see: a) A. Fürstner, K. Grela, C. Mathes, C. W. Lehmann, J. Am. Chem. Soc. 2000, 122, 11799-11805;
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For a discussion of our strategic goals see: A. Fürstner, Synlett 1999, 1523-1533.
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c) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069.
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i) S. C. Cho, P. H. Dussault, A. D. Lisec, E. C. Jensen, K. W. Nickerson, J. Chem. Soc. Perkin Trans. 1 1999, 193-196;
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m) J. Telser, R. Beumer, A. A. Bell, S. M. Ceccarelli, D. Monti, C. Gennari, Tetrahedron Lett. 2001, 42, 9187-9190.
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RCM can lead to the (E)-olefin even for an eight membered ring, cf.: D. Bourgeois, A. Pancrazi, L. Ricard, J. Prunet, Angew. Chem. 2000, 112, 741-744;
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For related reactions of deoxyribose with stabilized ylides see: a) K. C. Nicolaou, D. A. Nugiel, E. Couladouros, C.K. Hwang, Tetrahedron 1990, 46, 4517-4552;
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33751293527
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The same reaction in toluene at 80 °C was substantially less efficient (29% yield, E:Z = 6:1)
-
The same reaction in toluene at 80 °C was substantially less efficient (29% yield, E:Z = 6:1).
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f) A. Fürstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer, O. R. Thiel, Chem. Eur. J. 2001, 7, 3236-3253.
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