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Isabelle Bonnaventure, Angélique Fortier, Sébastien Goudreau, Vincent Lindsay, James Mousseau Synthesis Meeting Synthesis of Echinopine B May 13 th, 2008.

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Presentation on theme: "Isabelle Bonnaventure, Angélique Fortier, Sébastien Goudreau, Vincent Lindsay, James Mousseau Synthesis Meeting Synthesis of Echinopine B May 13 th, 2008."— Presentation transcript:

1 Isabelle Bonnaventure, Angélique Fortier, Sébastien Goudreau, Vincent Lindsay, James Mousseau Synthesis Meeting Synthesis of Echinopine B May 13 th, 2008

2 Retrosynthesis

3 Pauson-Khand Precursor’s Synthesis Yadav et al. J. Chem. Soc., Chem. Commun. 1990, 843-844 (a) Sharpless et al. J. Am. Chem. Soc. 1980, 102, 5974-5976 (b) Sharpless et al. Org. React. 1996, 48, 1-299 Smith et al. Org. React. 2003, 5, 1959-1962

4 Pauson-Khand Magnus, P. et al. J. Am. Chem. Soc. 1983, 105, 2477-2478

5 Cyclopropanation: Corey-Chaykovsky Rocket et al. Bull. Soc. Chim. Fr. 1974, 5-6, 888-894 Corey, Chaykovsky J. Am. Chem. Soc. 1965, 87, 1353-1364

6 Heck Precursor’s Synthesis

7

8 Heck Fu, G. C., et al. J. Am. Chem. Soc. 2007, 129, 11340-11341 Fu, G. C., et al. J. Am. Chem. Soc. 2006, 128, 5360-5361

9 Heck Fu, G. C., et al. J. Am. Chem. Soc. 2004, 126, 82-83 Danishefsky et al. Tet. Lett. 1993, 34, 7253-7256

10 Overview 18 steps

11 Pauson-Khand Greene, A. E., et al. J. Am. Chem. Soc. 1990, 112, 9388-9389


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