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Université de Montréal March 20th 2007

Theoretical Synthesis of Biyouyanagin A Maryon Ginisty Kim Laberge Miguel St-Onge David Marcoux Guillaume Barbe. Université de Montréal March 20th 2007. Retrosynthetic Analysis. Synthesis of R4. Synthesis of R4. Synthesis of R4. Synthesis of R4. Synthesis of R4. Synthesis of R4.

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Université de Montréal March 20th 2007

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  1. Theoretical Synthesis of Biyouyanagin AMaryon GinistyKim LabergeMiguel St-OngeDavid MarcouxGuillaume Barbe Université de Montréal March 20th 2007

  2. Retrosynthetic Analysis

  3. Synthesis of R4

  4. Synthesis of R4

  5. Synthesis of R4

  6. Synthesis of R4

  7. Synthesis of R4

  8. Synthesis of R4

  9. Synthesis of R4

  10. Synthesis of R4

  11. Synthesis of R5

  12. Synthesis of R5

  13. Synthesis of R5

  14. Synthesis of R5

  15. Synthesis of R3

  16. Synthesis of R3

  17. Synthesis of R2

  18. Synthesis of R1 • Thermodynamic enolization • All cis configuration • Tri-substituted alkene • Kinetic enolization (system conformation) • The conformation of the system may position suitably a methylene proton for kinetic cis,cis diene formation

  19. Synthesis of R1

  20. Synthesis of R1

  21. Synthesis of Biyouyanagin A

  22. Synthesis of Biyouyanagin A

  23. Synthesis of Biyouyanagin A

  24. Conclusion • Theoric total synthesis in 22 linear steps • Key Steps include NHK macrocyclisation and transannular [2+2] cycloaddition • Chiral auxiliaries approach (Myers and Meyers)

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