1. Synthesis of Biyouyanagin A
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
Radical Allylation

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

5. Retrosynthesis p-Allyl Substitution Enolate C-Acylation
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!