Total Synthesis of Communesins Jian-Zhou Huang

 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

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

Structures of the Communesins 1, Intrduction

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

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

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

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

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

23 reaction steps 3% overall yield

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

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

cross-aldol reaction

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

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

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

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

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

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

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

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

4, Conclusion

Thank You!

Oxidative Coupling Lindert, A. J. Am. Chem. Soc.1971, 93, Phil S. Baran, J. Am. Chem. Soc. 2004, 126,

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

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