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Guillaume Barbe Guillaume Pelletier Miguel St-Onge Sébastien Vanier

Guillaume Barbe Guillaume Pelletier Miguel St-Onge Sébastien Vanier. Stereoselective Synthesis of Echinopines A and B. Lab B. Université de Montréal May 13 th 2008. Strategies for Ring Formation. Strategies for Ring Formation. Strategies for Ring Formation. Strategies for Ring Formation.

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Guillaume Barbe Guillaume Pelletier Miguel St-Onge Sébastien Vanier

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  1. Guillaume BarbeGuillaume PelletierMiguel St-OngeSébastien Vanier Stereoselective Synthesis of Echinopines A and B Lab B Université de Montréal May 13th 2008

  2. Strategies for Ring Formation

  3. Strategies for Ring Formation

  4. Strategies for Ring Formation

  5. Strategies for Ring Formation

  6. Retrosynthetic Analysis

  7. Asymmetric Synthesis of Norbornenone

  8. Norbornenone Allylation

  9. Norbornenone Allylation

  10. Tandem Metathesis Key Step

  11. Tandem Metathesis Key Step

  12. Tandem Metathesis Key Step

  13. Tandem Metathesis Key Step

  14. Tandem Metathesis Key Step

  15. Tandem Metathesis Key Step

  16. Tandem Metathesis Key Step

  17. Tandem Metathesis Key Step

  18. Tandem Metathesis Key Step

  19. Alkyne Formation

  20. Alkyne Formation

  21. Alkyne Formation

  22. 7-exo-trig Radical Cyclization

  23. 7-exo-trig Radical Cyclization

  24. 7-exo-trig Radical Cyclization: Mechanism

  25. 7-exo-trig Radical Cyclization: Mechanism

  26. Allylic Alcohol Synthesis

  27. Allylic Alcohol Synthesis

  28. Chemoselective Cyclopropanation

  29. Chemoselective Cyclopropanation

  30. Conclusion • 17 steps stereoselective synthesis • Features tandem metathesis and radical cyclization as key steps • Only one protecting group (acetal) • Late incorporation of cyclopropane (stability)

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