asteltoxin s.l. schreiber 1983 - michigan state …...conclusion/summary •since discovery the...
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AsteltoxinS.L. Schreiber 1983
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Schreiber, S.L.; Hoveyda, A.H.; Wu, H.-J. J. Am. Chem. Soc. 1983, 105, 660.
The Beginning
2Ciamician, G.; Silber, P. Ber. Dtsch. Chem. Ges. 1908, 41, 1928.
Paterno, E.; Chieffi, G. Gazz. Chim. Ital. 1909, 39, 341
The Beginning contd.
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Cookson, R.C.; Crundwell, E.; Hudec, J. Chem. Ind. (London) 1958, 1003. Eaton, P.E.; Cole, T.W., Jr. J Am. Chem. Soc 1964, 86, 962
Eaton, P.E.; Cole, T.W., Jr. ibid. 1964, 86, 3157.
Paterno-Buchi reaction
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Paterno, E.; Chieffi, G. Gazz. Chim. Ital. 1909, 39, 341 Buchi, G.; Inman, C.G.; Lipinsky, E.S. J. Am. Chem. Soc. 1954, 76, 4327
Buchi, G.; Goldman, I.M. ibid. 1957, 79, 4741Schroeter, S.H.; Orlando, C.M., J. Org. Chem. 1969, 34, 1181
Schroeter, S.H. ibid. 1969, 34, 1188Maurizio, D.; Rocco R. Molecules 2013, 18, 11384-1142.
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Schreiber, S.L.; Hoveyda, A.H.; Wu, H.-J. J. Am. Chem. Soc. 1983, 105, 660.
6Schreiber, S.L.; Hoveyda, A.H.; Wu, H.-J. J. Am. Chem. Soc. 1983, 105, 660.
Retrobreakdown
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Total Synthesis
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11Grieco, P.A.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1976, 41, 1485
12Corey, E.J.; Hoover, D.J. Tetrahedron Lett. 1982, 23, 3463.
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Cram, D.J.; Abd Elhafez, F.A. J. Am Chem. Soc. 1952, 74, 5828Cram, D.J.; Kopecky, K.R. ibid. 1959, 81, 2748.
Marti-Castro, A.N, Chem. Rev. 2004, 104, 2939−3002
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Pummerer rearrangement 26-27
De Lucchi, O.; Miotti, U.’ Modena, G. Org React. (N.Y.) 1991, 40, 157Moiseenkov, A.M.; Dragan, V.A.; Veselovskii, V.V. Russ. Chem. Rev. (Engl. Transl.) 1991, 60, 643.
Smith, Laura H. S.; Coote, Susannah C.; Sneddon, Helen F.; Procte, David J.; Angew. Chem. Int. Ed. 2010, 49, 5832–5844
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Conclusion/Summary
• Since discovery the Paterno-Buchi process it hasbecome a tool used in highly oxygenated and stereochemically complex molecules
• It has been cited 94 times according to Web of Science.
• The feasibility and speed of the photo induced reaction makes it a perfect viable process for natural product synthesis.
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Recent total synthesis from Wayne State!
• Eom, K. D., Raman, J. V., Kim, H., & Cha, J. K. (2003). Total synthesis of (+)-asteltoxin. Journal of the American Chemical Society, 125(18), 5415-5421
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Acknowledgements
Dr. Maleczka
Walker Lab
Kio
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Questions?
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