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Synthesis of Biyouyanagin A Philippe Murphy Daniel Beaudoin Lucie Zimmer Christian Perreault

Introduction. Synthesis of Biyouyanagin A Philippe Murphy Daniel Beaudoin Lucie Zimmer Christian Perreault Capt’n Alex. Retrosynthesis. p -Allyl Substitution. Enolate C-Acylation. Retrosynthesis. p -Allyl Substitution. Enolate C-Acylation. p -Allyl Substitution. Radical Allylation.

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Synthesis of Biyouyanagin A Philippe Murphy Daniel Beaudoin Lucie Zimmer Christian Perreault

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  1. Introduction Synthesis of Biyouyanagin A Philippe Murphy Daniel Beaudoin Lucie Zimmer Christian Perreault Capt’n Alex

  2. Retrosynthesis p-Allyl Substitution Enolate C-Acylation

  3. Retrosynthesis p-Allyl Substitution Enolate C-Acylation p-Allyl Substitution Radical Allylation

  4. Retrosynthesis p-Allyl Substitution Enolate C-Acylation p-Allyl Substitution C-H Insertion Radical Allylation O-Alkylation

  5. Retrosynthesis p-Allyl Substitution Enolate C-Acylation p-Allyl Substitution C-H Insertion Radical Allylation O-Alkylation Diels-Alder Suzuki Coupling

  6. Preparing the Diels-Alder 1 Xu, D.; Li, Z.; Ma, S. Tetrahedron Lett. 2003, 44, 6343

  7. Preparing the Diels-Alder 1 Xu, D.; Li, Z.; Ma, S. Tetrahedron Lett. 2003, 44, 6343 2 Smith, N. D.; Goodman, M. Org. Lett. 2003, 5, 1035 3 (DHQD)2-PHAL and K2OsO2(OH)4

  8. Diels-Alder key step

  9. Diels-Alder key step

  10. Diels-Alder key step

  11. Why the D-A should work

  12. Diels-Alder key step

  13. Retrosynthesis C-H Insertion O-Alkylation

  14. Tetrahydrofuran Ring-Closure

  15. Tetrahydrofuran Ring-Closure

  16. Retrosynthesis p-Allyl Substitution Radical Allylation

  17. Cyclobutane Formation

  18. Double Bond Reduction

  19. Double Bond Reduction

  20. Retrosynthesis p-Allyl Substitution Enolate C-Acylation

  21. Putting the Side Chain in Place

  22. Final Cyclization

  23. Final Cyclization

  24. Retrospective 19 Steps in Total!

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