Literature Meeting February, 7th, 2005 Jean-Manuel Cloarec

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Presentation transcript:

Literature Meeting February, 7th, 2005 Jean-Manuel Cloarec Norzoanthamine Literature Meeting February, 7th, 2005 Jean-Manuel Cloarec

Zoanthamine Alkaloids Family

Zoanthamine Alkaloids Family

Total Synthesis of Norzoanthamine Sakai, M.; Sasaki, M.; Tanino, K. Miyashita, M. Tetrahedron Lett. 2002, 43, 1705-1708. Miyashita, M.; Sasaki, M.; Hattori, I.; Sakai, M.; Tanino, K. Science 2004, 305, 495-499.

Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026. Contribution of Williams Retrosynthetic Analysis A & B Ring Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026.

Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026. Contribution of Williams Retrosynthetic Analysis A & B Ring Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026.

Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026. Contribution of Williams Retrosynthetic Analysis A & B Ring Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026.

Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026. Contribution of Williams Retrosynthetic Analysis A & B Ring Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026.

Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026. Contribution of Williams Retrosynthetic Analysis A & B Ring Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026.

Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026. Contribution of Williams Retrosynthetic Analysis A & B Ring Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026.

Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026. Contribution of Williams Retrosynthetic Analysis A & B Ring Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026.

Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026. Norzoanthamine Contribution of Williams Conclusion Williams, D. R. ; Brugel, T. A. Org. Lett. 2000, 2, 1023-1026.

Contribution of Theodorakis Retrosynthetic Analysis A, B & C Ring Ghosh, S.; Rivas, F.; Fisher, D.: Gonzalez, M. A.: Theodorakis, E. A. Org. Lett. 2004, 6, 941-944.

Norzoanthamine Contribution of Theodorakis A, B & C Ring Ghosh, S.; Rivas, F.; Fisher, D.: Gonzalez, M. A.: Theodorakis, E. A. Org. Lett. 2004, 6, 941-944.

Norzoanthamine Contribution of Theodorakis A, B & C Ring Ghosh, S.; Rivas, F.; Fisher, D.: Gonzalez, M. A.: Theodorakis, E. A. Org. Lett. 2004, 6, 941-944.

Norzoanthamine Contribution of Theodorakis A, B & C Ring Ghosh, S.; Rivas, F.; Fisher, D.: Gonzalez, M. A.: Theodorakis, E. A. Org. Lett. 2004, 6, 941-944.

Norzoanthamine Contribution of Theodorakis A, B & C Ring Ghosh, S.; Rivas, F.; Fisher, D.: Gonzalez, M. A.: Theodorakis, E. A. Org. Lett. 2004, 6, 941-944.

Norzoanthamine Contribution of Theodorakis Conclusion Ghosh, S.; Rivas, F.; Fisher, D.: Gonzalez, M. A.: Theodorakis, E. A. Org. Lett. 2004, 6, 941-944.

Norzoanthamine Contribution of Hirama Retrosynthetic Analysis Hirama, M. Oguri, H.; Hirai, G. Chem. Lett. 1999, 141-142. For a catalytic asymmetric DA mechanistic study: Moharram, S. M.; Hirai, G.; Koyama, K.; Oguri, H.; Hiyama, M,Tetrahedron Lett. 2000, 41, 6669-6673.

Hirama, M. Oguri, H.; Hirai, G. Chem. Lett. 1999, 141-142. Norzoanthamine Contribution of Hirama Retrosynthetic Analysis Hirama, M. Oguri, H.; Hirai, G. Chem. Lett. 1999, 141-142.

Hirama, M. Oguri, H.; Hirai, G. Chem. Lett. 1999, 141-142. Norzoanthamine Contribution of Hirama C Ring Hirama, M. Oguri, H.; Hirai, G. Chem. Lett. 1999, 141-142.

Hirama, M. Oguri, H.; Hirai, G. Chem. Lett. 1999, 141-142. Norzoanthamine Contribution of Hirama C Ring Hirama, M. Oguri, H.; Hirai, G. Chem. Lett. 1999, 141-142.

Hirama, M. Oguri, H.; Hirai, G. Chem. Lett. 1999, 141-142. Norzoanthamine Contribution of Hirama Conclusion Hirama, M. Oguri, H.; Hirai, G. Chem. Lett. 1999, 141-142.

Norzoanthamine Contribution of Kobayashi Hemi-Aminal Core Retrosynthetic Analysis Hikage, N.; Furukawa, H.; Takao, K.; Kobayashi, S. Tetrahedron Lett. 1998, 39, 6237-6240.

Norzoanthamine Contribution of Kobayashi Hemi-Aminal Core Hikage, N.; Furukawa, H.; Takao, K.; Kobayashi, S. Tetrahedron Lett. 1998, 39, 6237-6240.

Norzoanthamine Contribution of Kobayashi Hemi-Aminal Core Hikage, N.; Furukawa, H.; Takao, K.; Kobayashi, S. Tetrahedron Lett. 1998, 39, 6237-6240.

Norzoanthamine Contribution of Kobayashi Hemi-Aminal Core Hikage, N.; Furukawa, H.; Takao, K.; Kobayashi, S. Tetrahedron Lett. 1998, 39, 6237-6240.

Norzoanthamine Contribution of Kobayashi Hemi-Aminal Core Hikage, N.; Furukawa, H.; Takao, K.; Kobayashi, S. Tetrahedron Lett. 1998, 39, 6237-6240.

Norzoanthamine Contribution of Kobayashi Hemi-Aminal Core Hikage, N.; Furukawa, H.; Takao, K.; Kobayashi, S. Tetrahedron Lett. 1998, 39, 6237-6240.

Norzoanthamine Contribution of Kobayashi Hemi-Aminal Core Hikage, N.; Furukawa, H.; Takao, K.; Kobayashi, S. Tetrahedron Lett. 1998, 39, 6237-6240.

Norzoanthamine Contribution of Kobayashi Hemi-Aminal Core Hikage, N.; Furukawa, H.; Takao, K.; Kobayashi, S. Tetrahedron Lett. 1998, 39, 6237-6240.

Norzoanthamine Contribution of Kobayashi Conclusion Hikage, N.; Furukawa, H.; Takao, K.; Kobayashi, S. Tetrahedron Lett. 1998, 39, 6237-6240.

Williams, D.R.; Cortez, G. S. Tetrahedron Lett. 1998, 39, 2675-2678. Norzoanthamine Contribution of Williams Hemi-Aminal Core Retrosynthetic Analysis Williams, D.R.; Cortez, G. S. Tetrahedron Lett. 1998, 39, 2675-2678.

Williams, D.R.; Cortez, G. S. Tetrahedron Lett. 1998, 39, 2675-2678. Norzoanthamine Contribution of Williams Hemi-Aminal Core Williams, D.R.; Cortez, G. S. Tetrahedron Lett. 1998, 39, 2675-2678.

Williams, D.R.; Cortez, G. S. Tetrahedron Lett. 1998, 39, 2675-2678. Norzoanthamine Contribution of Williams Hemi-Aminal Core Williams, D.R.; Cortez, G. S. Tetrahedron Lett. 1998, 39, 2675-2678.

Williams, D.R.; Cortez, G. S. Tetrahedron Lett. 1998, 39, 2675-2678. Norzoanthamine Contribution of Williams Hemi-Aminal Core Williams, D.R.; Cortez, G. S. Tetrahedron Lett. 1998, 39, 2675-2678.

Williams, D.R.; Cortez, G. S. Tetrahedron Lett. 1998, 39, 2675-2678. Norzoanthamine Contribution of Williams Hemi-Aminal Core Williams, D.R.; Cortez, G. S. Tetrahedron Lett. 1998, 39, 2675-2678.

Williams, D.R.; Cortez, G. S. Tetrahedron Lett. 1998, 39, 2675-2678. Norzoanthamine Contribution of Williams Hemi-Aminal Core Conclusions Williams, D.R.; Cortez, G. S. Tetrahedron Lett. 1998, 39, 2675-2678.

Norzoanthamine Contributions to the Synthesis: Conclusions

Norzoanthamine Total Synthesis Sakai, M.; Sasaki, M.; Tanino, K. Miyashita, M. Tetrahedron Let. 2002, 43, 1705-1708. Miyashita, M.; Sasaki, M.; Hattori, I.; Sakai, M.; Tanino, K. Science 2004, 305, 495-499.

Retrosynthetic Analysis

Construction of the ABC Moiety 1 Mutti, S.; Daubié, C.; Decalogne, F.; Fournier, R..; Rossi,P. Tetrahedron Lett. 1996, 37, 3125-3128. 2 Yamamoto K.; Yamamoto N. Chem. Lett. 1989, 1149-1152.

Yamamoto K.; Yamamoto N. Chem. Lett. 1989, 1149-1152. Yamamoto Epoxidation Yamamoto K.; Yamamoto N. Chem. Lett. 1989, 1149-1152.

Construction of the ABC Moiety Mutti, S.; Daubié, C.; Decalogne, F.; Fournier, R..; Rossi,P. Tetrahedron Lett. 1996, 37, 3125-3128.

Construction of the ABC Moiety Piers, E.; Morton, H. E. J. Org. Chem. 1980, 45, 4263–4264.. . TMSCl accelarated conjugate addition, see: Nakamura E.; Matsuzawa, S.; Horiguchi, Y.; Kuwajima, I Tetrahedron Lett., 1986, 34, 4029-4032.

Construction of the ABC Moiety

Construction of the ABC Moiety Sakai, M.; Sasaki, M.; Tanino, K. Miyashita, M. Tetrahedron Lett. 2002, 43, 1705-1708.

Construction of the ABC Moiety Ojima, I.; Kogure, T.; Nagai, Y. Tetrahedron Lett. 1972, 13, 5035-5038.

Construction of the ABC Moiety

Construction of the ABC Moiety For related oxidation of furans rings using Katsumura protocol see: Faulkner, D. J.; Kernan, M. R. J. Org. Chem. 1988, 53, 2773-2776.

Construction of the ABC Moiety

Construction of the DEFG Moiety K-selectride: potassium tri-sec-butylborohydride DiBALH: diisobutylaluminium hydride

Construction of the DEFG Moiety Molybdenum oxidation: Trost B. m.; Masuyama, Y. Tetrahedron Lett. 1984, 25, 173-176.

Construction of the DEFG Moiety DMPU: 1,3 dimethyl 3,4,5,6 tetrahydro-2(1H)-pyrimidinone alias N,N' DiMethylPropyleneUrea

Construction of the DEFG Moiety

Construction of the DEFG Moiety For use of deuterium isotope effect in natural product synthesis: Clive D. L. J. ; et al, J. Am. Chem. Soc. 1994, 116, 11275-11286. Vedejs E.; Little, J. J. Am. Chem. Soc. 2002, 124, 748-749.

Construction of the DEFG Moiety

Construction of the DEFG Moiety

Final Critical bis Amino-Acetalization: Construction of the D & E Ring

Total Synthesis of Norzoanthamine: Conclusion The stereoselective total synthesis of Norzoanthamine is reported in 41 steps, overall yield: 3.5 % (average of 92 % each step) Sakai, M.; Sasaki, M.; Tanino, K. Miyashita, M. Tetrahedron Lett. 2002, 43, 1705-1708. Miyashita, M.; Sasaki, M.; Hattori, I.; Sakai, M.; Tanino, K. Science 2004, 305, 495-499.