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Total Synthesis of Epothilone A: The Olefin Metathesis Approach

Total Synthesis of Epothilone A: The Olefin Metathesis Approach. Zhen Yang, Yun He, Dionisios Vourloumis, Hans Vallberg, and K. C. Nicolaou Angew. Chem. Int. Ed. 1997, 36, 166-168 Presented by: Steven Rossi April 03, 2012. K. C. Nicolaou. 1946: Born in Karavas, Cyprus

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Total Synthesis of Epothilone A: The Olefin Metathesis Approach

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  1. Total Synthesis of Epothilone A: The Olefin Metathesis Approach Zhen Yang, Yun He, Dionisios Vourloumis, Hans Vallberg, and K. C. Nicolaou Angew. Chem. Int. Ed. 1997, 36, 166-168 Presented by: Steven Rossi April 03, 2012

  2. K. C. Nicolaou • 1946: Born in Karavas, Cyprus • 1969: B.S. University of London • 1972: Ph.D. under F. Sondheimer and P.J. Garret at Univeristy of London • 1972: Postdoc T. J. Katz • 1974: Postdoc E. J. Corey • 1976: Joined the Faculty at UPenn • Sloan Fellowship while at UPenn • 1989: Joined the faulty at UC: San Diego • 1989: Joined the Scripps Research Institute • Currently Active at both institutions

  3. Epothilone A • Isolated from Sorangium Cellulosum, soil dwelling myxobacteria • Structure determined in 1996 via X-Ray • Prevent cancer cell division • Similar in biological activity to Taxens, but milder side effects with higher efficiency • Epothilone A-F have been isolated to date

  4. Epothilones A: R= H C: R= H B: R= Me D: R= Me E: R= H F: R= Me

  5. Epothilone A

  6. Previous Synthesis • Danishefsky (1996) • Schinzer (1997) • Mulzer (2000) • Carreira (2001)

  7. Retrosynthesis

  8. Synthesis of Fragment A

  9. Synthesis of Fragment B J. Am. Chem. Soc. 1997, 119, 7960-7973

  10. Synthesis of Fragment C

  11. Fragment Additions

  12. Final Products

  13. Conclusions • Vital Step: Intramolecular Olefin Metathesis • Fairly Steroselective • Relatively short and high yielding Total Synthesis

  14. Questions?

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