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F. In Comprehensive Organic Synthesis; Trost, B. ; Pergamon Press: Oxford, 1991; Vol. 4. [R] Heck, R. F. Org. React. (N. ) 1982, 27, 345. [R] Daves, G. ; Hallberg, A. Chem Rev. 1989, 89, 1433. ; Meyer, F. E. Angew. , Int. Ed Engl. 1994, 33, 2379. [R] de Meijere, A, Braese, S. In Transition Metal Catalyzed Reactions; Davies S. ; Blackwell Science: Oxford, 1999. ; Candiani, I. Ace. Chem. Res. 1995, 28, 2. [R] Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. ; Jai Press Inc: Greenwich, CT, 1996; Vol.

Wiley-VCH: New York, 1998. ; Boden, C. D. ; Kojima, A. Tetrahedron, 1997, 53, 7371. [R] Overman, L. E. Pure Appl. Chem. 1994, 66, 1423. [R] Link, J. ; Overman, L. E. , Stang, P. ; Wiley-VCH: New York, 1998. [R] Link, J. ; Overman, L. E. Chemtech 1998, 28, 19. [R] Gibson, S. ; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447. [R] Reetz, M. T. In Metal-Catalyzed Reactions; Davies, S. : Oxford, 1999. [R] Beletskaya, I. ; Cheprakov, A. V. Chem. Rev. 2000,100, 3009. [R] Dounay, A. ; Overman, L. E.

CISi(OEt)3 3. 2 equiv) THF, 30 °C, 48-72 h "" 66-98% Si(OEt) 3 43 Chapter 1. Organometallics Applications in Natural Products The Hiyama cross-coupling reaction has not been highly represented in the preparation of natural products compared to the Negishi, Stille, and Suzuki reactions. DeShong utilized this key step in synthetic studies towards several natural products. 40 Elaboration of 54 to phenanthrol 55 was accomplished in six steps. Finally phenanthrol ring expansion provided racemic jV-acetyl colchinol-0-methyl ether (56).

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