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Total Synthesis of BE-43472B

Total Synthesis of BE-43472B. PhD Work with Prof. André B. Charette. The Scripps Research Institute La Jolla, California. The Scripps Research Institute. World's largest, private non-profit biomedical research facility Founded in 1961 by Frank Dixon, M.D. 289 Faculty members

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Total Synthesis of BE-43472B

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  1. Total Synthesis of BE-43472B

  2. PhD Work with Prof. André B. Charette

  3. The Scripps Research InstituteLa Jolla, California

  4. The Scripps Research Institute World's largest, private non-profit biomedical research facility Founded in 1961 by Frank Dixon, M.D. 289 Faculty members 815 Postdoctoral fellows 235 Graduate students 1,500 technical and administrative support personnel

  5. The Scripps Research Institute K. C. Nicolaou - Chairman of chemistry dept. Barry K. Sharpless - Nobel laureate Phil S. Baran Dale Boger Carlos F. Barbas III Jin-Quan Yu Albert Eschenmoser Kim D. Jenda Richard Lerner Peter Schultz Julius Rebek Jr. Director, Skaggs Institute for Chemical Biology

  6. BE-43472B Isolated from marine streptomycete collected in Puerto Rico Chrysophanol dimer linked in tetrahydrofuran rings with an incorporated acetaldehyde molecule New structural class among known antimicrobial agents Socha, A. M.; Rowley D. C. et al. J. Nat. Prod. 2006, 69, 1070.

  7. BE-43472B Retrosynthesis

  8. Model Studies

  9. Model Studies

  10. Chrysophanol Derivative Synthesis

  11. Chrysophanol Derivative Synthesis Hauser annulation

  12. Chiral Diene Synthesis and Diels-Alder Reaction

  13. E-Reduction of Propargylic Alcohol 1st report by Corey in 1967 (LiAlH4 + 2 MeOH) Red-Al introduced 15 years later by Denmark

  14. Chiral Diene Synthesis and Diels-Alder Reaction

  15. Ether 1,4-Elimination

  16. Chiral Diene Synthesis and Diels-Alder Reaction

  17. Quinone Acceptor Synthesis – Initial Hopes

  18. Quinone Acceptor Synthesis – Initial Hopes

  19. Quinone Acceptor Synthesis – Initial Hopes

  20. Quinone Michael Acceptor Synthesis

  21. Quinone Michael Acceptor Synthesis

  22. Quinone Michael Acceptor Synthesis hydrolysis happened in purification

  23. Quinone Michael Acceptor Synthesis hydrolysis happened in purification

  24. Quinone Michael Acceptor Synthesis hydrolysis happened in purification

  25. Quinone Michael Acceptor Synthesis

  26. Fragments Coupling and Aromatization

  27. Fragments Coupling Attempts Real system From model studies

  28. Fragments Coupling and Aromatization

  29. Fragments Coupling and Aromatization

  30. 1,4-Addition Attempts caused by in situ reducing metal?

  31. 1,4-Addition Attempts

  32. Friedel-Crafts Fragments Coupling Attempts

  33. New Strategy

  34. Reversal of the Diene Electronics

  35. Diene Synthesis

  36. Diels-Alder with New Diene

  37. Diels-Alder with New Diene

  38. Completion of the Synthesis

  39. Photochemical Epoxide Rearrangement Nicolaou, K. C.; Lim, Y.-H.; Becker, J.; Lemire, A.; Neubauer, T.; Montero, A. J. Am. Chem. Soc. 2009, 131, 14812.

  40. Acknowledgments Prof. K. C. Nicolaou Research group members Yee-Hwee Lim Jochen Becker

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