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Total Synthesis of Epothilone A: The Olefin Metathesis Approach

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Presentation on theme: "Total Synthesis of Epothilone A: The Olefin Metathesis Approach"— Presentation transcript:

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, 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,

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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