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

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Presentation on theme: "Literature Meeting February, 7th, 2005 Jean-Manuel Cloarec"— Presentation transcript:

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

2 Zoanthamine Alkaloids Family

3 Zoanthamine Alkaloids Family

4 Total Synthesis of Norzoanthamine
Sakai, M.; Sasaki, M.; Tanino, K. Miyashita, M. Tetrahedron Lett. 2002, 43, Miyashita, M.; Sasaki, M.; Hattori, I.; Sakai, M.; Tanino, K. Science 2004, 305,

5 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,

6 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,

7 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,

8 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,

9 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,

10 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,

11 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,

12 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,

13 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,

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

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

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

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

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

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

20 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,

21 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,

22 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,

23 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,

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

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

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

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

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

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

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

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

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

33 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,

34 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,

35 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,

36 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,

37 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,

38 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,

39 Norzoanthamine Contributions to the Synthesis: Conclusions

40 Norzoanthamine Total Synthesis
Sakai, M.; Sasaki, M.; Tanino, K. Miyashita, M. Tetrahedron Let. 2002, 43, Miyashita, M.; Sasaki, M.; Hattori, I.; Sakai, M.; Tanino, K. Science 2004, 305,

41 Retrosynthetic Analysis

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

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

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

45 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,

46 Construction of the ABC Moiety

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

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

49 Construction of the ABC Moiety

50 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,

51 Construction of the ABC Moiety

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

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

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

55 Construction of the DEFG Moiety

56 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, Vedejs E.; Little, J. J. Am. Chem. Soc. 2002, 124,

57 Construction of the DEFG Moiety

58 Construction of the DEFG Moiety

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

60 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, Miyashita, M.; Sasaki, M.; Hattori, I.; Sakai, M.; Tanino, K. Science 2004, 305,

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