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Lab A: Vincent Lindsay, Cyril Nicolas, Pascal Cérat and Sébastien Goudreau Synthesis Meeting Proposed Total Synthesis of Haliclonin A November 7 th, 2009.

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Presentation on theme: "Lab A: Vincent Lindsay, Cyril Nicolas, Pascal Cérat and Sébastien Goudreau Synthesis Meeting Proposed Total Synthesis of Haliclonin A November 7 th, 2009."— Presentation transcript:

1 Lab A: Vincent Lindsay, Cyril Nicolas, Pascal Cérat and Sébastien Goudreau Synthesis Meeting Proposed Total Synthesis of Haliclonin A November 7 th, 2009

2 2 Retrosynthesis

3 3 Phosphonate: Tet. Lett. 1991, 32, 5907 Synthesis of Diels-Alder Precursors HWE: Paintner, F.F.; Bauschke, G.; Polborn, K. Tet. Lett. 2003, 44, 2549

4 4 Diels-Alder

5 5 Quaternary Center

6 6 Macrocyclisation

7 7 2nd Macrocycle Chain

8 8 vinyl bromide: Tet. Lett. 2004, 45, 2563

9 9 Addition of the 2nd Macrocycle Chain

10 10 Macrocyclisation & Epoxydation

11 11 Double Bond: Radical Deoxygenation-Epoxyde Opening

12 12 Epoxyde Opening favorednot favored

13 13 Final steps 27 steps

14 14 Retrosynthesis

15 15

16 16 Epoxyde Opening favorednot favored


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