1. Total Synthesis of Communesins Jian-Zhou Huang 2012-10-27

2.  1, Intrduction  2, Model Study 2.1 model study by Stoltz 2.2 model study by Funk  3, Total Synthesis 3.1 Total Synthesis by Yong Qin 3.2 Total Synthesis by Weinreb 3.3 Total Synthesis by Dawei Ma 3.4 Total Synthesis by Funk  4, Conclusion Contents

3. 1, Intrduction Ficus microcarpa 榕树 In 2001, Hemscheidt In 2003, Stoltz and Funk Thomas K. Hemscheidt, J. Org. Chem. 2001, 66, 8717 B. M. Stoltz, Tetrahedron Lett. 2003, 44, 1203 R. L. Funk, Org. Lett. 2003, 5, 3169

4. Structures of the Communesins 1, Intrduction

6. 2, Model Study 2.1 Biomimetic model study by Stoltz B. M. Stoltz, Tetrahedron Lett. 2003, 44, 1203

7. R. L. Funk, Org. Lett. 2003, 5, 3169 2.2, Model study by Funk

8. 3.1, First Total Synthesis of Communesins F by Yong Qin Yong Qin, J. Am. Chem. Soc. 2007, 129, 13794-13795 Retrosynthetic analysis

9. 3.1 Total Synthesis of Communesins F by Yong Qin Yong Qin, J. Am. Chem. Soc. 2007, 129, 13794 Yong Qin, Org. Lett. 2006, 8, 2187 Staudinger reaction

10. Yong Qin, J. Am. Chem. Soc. 2007, 129, 13794

11. 23 reaction steps 3% overall yield

12. 3.2 Total Synthesis by Weinreb Steven M. Weinreb, Angew. Chem. Int. Ed. 2010, 49, 2000 –2003 Suzuki-Miyaura reaction

13. Steven M. Weinreb, Angew. Chem. Int. Ed. 2010, 49, 2000 –2003

14. cross-aldol reaction

15. Steven M. Weinreb, Angew. Chem. Int. Ed. 2010, 49, 2000 –2003 30 reaction steps

16. Dawei Ma, J. Am. Chem. Soc. 2010, 132, 13226–13228 3.3 Total Synthesis by Dawei Ma Retrosynthetic analysis

17. Dawei Ma, J. Am. Chem. Soc. 2010, 132, 13226–13228 3.3 Total Synthesis by Dawei Ma

18. Dawei Ma, J. Am. Chem. Soc. 2010, 132, 13226–13228

19. Angew. Chem. Int. Ed. 2011, 50, 12008 –12011 Communesins A and B : 19 reaction steps 6 % overall yield

20. Retrosynthetic analysis Raymond L. Funk, J. Am. Chem. Soc. 2012, 134, 16941−16943 3.4 Total Synthesis by Funk

21. Raymond L. Funk, J. Am. Chem. Soc. 2012, 134, 16941−16943 3.4 Total Synthesis by Funk

22. Raymond L. Funk, J. Am. Chem. Soc. 2012, 134, 16941−16943 15reaction steps 6.7% overall yield

23. 4, Conclusion

24. Thank You!

25. Oxidative Coupling Lindert, A. J. Am. Chem. Soc.1971, 93, 4605-4606 Phil S. Baran, J. Am. Chem. Soc. 2004, 126, 7450-7451

26. M. E. Hermes,J. Am. Chem. Soc., 1964, 86, 4506

27. Staudinger reaction Mechanism The Staudinger reaction or Staudinger reduction is a chemical reaction in which the combination of an azide with a phosphine or phosphiteproduces an iminophosphorane intermediate Combined with the hydrolysis of the aza-ylide to produce a phosphine oxide and an amine, this reaction is a mild method of reducing an azide to an amine. Triphenylphosphine is commonly used as the reducing agent, yielding triphenylphosphine oxide as the side product in addition to the amine