Total Synthesis of ( ‒ )-Colombiasin A and ( ‒ )-Elisapterosin B by two different approaches A presentation by Guillaume Pelletier April 27 th 2012.

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Presentation transcript:

Total Synthesis of ( ‒ )-Colombiasin A and ( ‒ )-Elisapterosin B by two different approaches A presentation by Guillaume Pelletier April 27 th 2012

Structural and biological analysis These molecules are additions to the family of diterpenes from the gorgonian octacoral Pseudopterogorgia elisabethae (isolated by Rodriguez et al. in early 2000) Possess potential antiplasmodial activity against plasmodium falciparum, the parasite responsible for the most severe forms of malaria and is an in vitro inhibitor of Mycobacterium tuberculosis H37Rb Total synthesis by many groups : Harrowven (2005, ■ and ■ ), Nicolaou (2001, ■), Rychnovsky (2003, ■ and ■), Rawal (2003, ■ ), Davies (2006, ■ ), Jacobsen and Boezio, A. A. (2005, ■ and ■) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45,

Various approaches to the targets Harrowvenm D. C.; Pascoe, D. D.; Demurtas, D.; Bourne, H. O. Angew. Chem., Int. Ed. 2005, 44, Waizumi, N.; Stankovic, A. R.; Rawal, V. R. J. Am. Chem. Soc. 2003, 125,

Harrowven’s approach to ( ‒ )- Colombiaisin A Harrowvenm D. C.; Pascoe, D. D.; Demurtas, D.; Bourne, H. O. Angew. Chem., Int. Ed. 2005, 44,

Harrowven’s approach to ( ‒ )- Colombiaisin A Harrowvenm D. C.; Pascoe, D. D.; Demurtas, D.; Bourne, H. O. Angew. Chem., Int. Ed. 2005, 44,

Harrowven’s approach to ( ‒ )- Colombiaisin A Brown, H. C.; Singaram, B. Acc. Chem. Res. 1988, 21, Brown, H. C.; Ramachandran, P. V. J. Organomet. Chem. 1995, 500, Matteson, D. S. Synthesis 1996,

Harrowven’s approach to ( ‒ )- Colombiaisin A Brown, H. C.; Singaram, B. Acc. Chem. Res. 1988, 21, Brown, H. C.; Ramachandran, P. V. J. Organomet. Chem. 1995, 500, Matteson, D. S. Synthesis 1996,

Harrowven’s approach to ( ‒ )- Colombiaisin A Harrowvenm D. C.; Pascoe, D. D.; Demurtas, D.; Bourne, H. O. Angew. Chem., Int. Ed. 2005, 44,

Harrowven’s approach to ( ‒ )- Colombiaisin A Harrowvenm D. C.; Pascoe, D. D.; Demurtas, D.; Bourne, H. O. Angew. Chem., Int. Ed. 2005, 44,

Kocienski’s modification of Julia olefination (BT sulfone) Baudin, J. B.; Hareau, G.; Julia, S. H.; Lorne, R.; Ruel, O. Bull. Chim. Soc. Fr. 1993, 130, Smith, N. D.; Kocienski, P. J.; Street, D. A. S. Synthesis 1996,

Kocienski’s modification of Julia olefination (BT sulfone) Baudin, J. B.; Hareau, G.; Julia, S. H.; Lorne, R.; Ruel, O. Bull. Chim. Soc. Fr. 1993, 130, Smith, N. D.; Kocienski, P. J.; Street, D. A. S. Synthesis 1996,  Cyclic (Chelate) TS favoured for non-polar solvent, small counter-ions (Li)  Open TS favoured for polar solvents, large counter-ions (K)

Kocienski’s modification of Julia olefination (BT sulfone) Charette, A. B.; Lebel, H. J. Am. Chem. Soc. 1996, 118,  Cyclic (Chelate) TS favoured for non-polar solvent, small counter-ions (Li)  Open TS favoured for polar solvents, large counter-ions (K)

Harrowven’s approach to ( ‒ )- Colombiaisin A Harrowvenm D. C.; Pascoe, D. D.; Demurtas, D.; Bourne, H. O. Angew. Chem., Int. Ed. 2005, 44,

Modified Bamford-Stevens (Shapiro) olefination Harrowvenm D. C.; Pascoe, D. D.; Demurtas, D.; Bourne, H. O. Angew. Chem., Int. Ed. 2005, 44, Reed, M. W.; Pollart, D. J.; Perri, S. T.; Foland, L. D.; Moore, H. W. J. Org. Chem. 1988, 53, 2477 – Shapiro, R. H. Org. React. 1976, 26,

Casanova, J.; Waegell, B. Bull. Chim. Soc. Fr. 1975, Nickon, A.; Bronfenbrenner, J. K. J. Am. Chem. Soc. 1982, 104, Bamford-Stevens olefination in protic and aprotic solvents

Harrowven’s approach to ( ‒ )- Colombiaisin A Harrowvenm D. C.; Pascoe, D. D.; Demurtas, D.; Bourne, H. O. Angew. Chem., Int. Ed. 2005, 44,

Moore rearrangement of vinylcyclobutene to hydroquinone Harrowvenm D. C.; Pascoe, D. D.; Demurtas, D.; Bourne, H. O. Angew. Chem., Int. Ed. 2005, 44, Karlsson, J. O.; Nguyen, N. V.; Foland, L. D.; Moore, H. W. J. Am. Chem. Soc. 1985, 107, Perri, S. T.; Dyke, H. J.; Moore, H.W. J. Org. Chem. 1989, 54,

Harrowven’s approach to ( ‒ )- Colombiaisin A Harrowvenm D. C.; Pascoe, D. D.; Demurtas, D.; Bourne, H. O. Angew. Chem., Int. Ed. 2005, 44, To be continued…

Rawal’s approach to ( ‒ )- Elisapterosin B Waizumi, N.; Stankovic, A. R.; Rawal, V. R. J. Am. Chem. Soc. 2003, 125,

Diazotization with HNO 2 Carey, F. A.; Sundberg, R. J. in “Advanced Organic Chemistry”, Springer, ed.; 4th Edition, Chap.

Rawal’s approach to ( ‒ )- Elisapterosin B Waizumi, N.; Stankovic, A. R.; Rawal, V. R. J. Am. Chem. Soc. 2003, 125, Negishi, E.; Bagheri, V.; Chatterjee, S.; Luo, F. T.; Miller, J. A.; Stoll, A. T. Tetrahedron Lett. 1983, 24,

Rawal’s approach to ( ‒ )- Elisapterosin B Waizumi, N.; Stankovic, A. R.; Rawal, V. R. J. Am. Chem. Soc. 2003, 125, Negishi, E.; Bagheri, V.; Chatterjee, S.; Luo, F. T.; Miller, J. A.; Stoll, A. T. Tetrahedron Lett. 1983, 24,

Rawal’s approach to ( ‒ )- Elisapterosin B Waizumi, N.; Stankovic, A. R.; Rawal, V. R. J. Am. Chem. Soc. 2003, 125,

Seyfert-Gilbert alkynylation Waizumi, N.; Stankovic, A. R.; Rawal, V. R. J. Am. Chem. Soc. 2003, 125, Seyferth, D.; Marmor, R. S.; Hilbert, P. J. Org. Chem. 1971, 36, Colvin, E. W.; Hamill, B. J. J. Chem. Soc., Chem. Commun.1973, Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1979, 44,

Rawal’s approach to ( ‒ )- Elisapterosin B Waizumi, N.; Stankovic, A. R.; Rawal, V. R. J. Am. Chem. Soc. 2003, 125,

Pinacol-type rearrangment of ketal Tsuchihashi, G., Kitajima, K., Mitamura, M. Tetrahedron Lett. 1981, 22, Honda, Y.; Ori, A.; Tsuchihashi, G. Bull. Chem. Soc. Jpn. 1987, 60,

Rawal’s approach to ( ‒ )- Elisapterosin B Waizumi, N.; Stankovic, A. R.; Rawal, V. R. J. Am. Chem. Soc. 2003, 125,

Rawal’s approach to ( ‒ )- Elisapterosin B Waizumi, N.; Stankovic, A. R.; Rawal, V. R. J. Am. Chem. Soc. 2003, 125,

Rawal’s approach to ( ‒ )- Elisapterosin B Waizumi, N.; Stankovic, A. R.; Rawal, V. R. J. Am. Chem. Soc. 2003, 125,

Salcomine catalyzed aerobic oxidation of phenol Van Dort, H. M.; Geursen, H. J. Recl. Trav. Chim. Pays-Bas 1967, 86, Parker, K. A.; Petraitis, J. J. Tetrahedron Lett. 1981, 22,

Rawal’s approach to ( ‒ )- Elisapterosin B Waizumi, N.; Stankovic, A. R.; Rawal, V. R. J. Am. Chem. Soc. 2003, 125,

Endo-selective Diels-Alder Waizumi, N.; Stankovic, A. R.; Rawal, V. R. J. Am. Chem. Soc. 2003, 125,

Rawal’s approach to ( ‒ )- Elisapterosin B Waizumi, N.; Stankovic, A. R.; Rawal, V. R. J. Am. Chem. Soc. 2003, 125,

CAN mediated oxidative cyclisation Waizumi, N.; Stankovic, A. R.; Rawal, V. R. J. Am. Chem. Soc. 2003, 125, Zanoni, G.;Franzini, M. Angew. Chem., Int. Ed. 2004, 43,

( ‒ )- Colombiaisin A to ( ‒ )-Elisapterosin B with BF 3 OEt 2 Boezio, A. A.; Jarvo, E. R.; Lawrence, B. M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44,

( ‒ )- Colombiaisin A to ( ‒ )-Elisapterosin B with BF 3 OEt 2 Boezio, A. A.; Jarvo, E. R.; Lawrence, B. M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44, Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45,