enantioselective total syntheses of manzamine a and related alkaloids n.
Skip this Video
Loading SlideShow in 5 Seconds..
Enantioselective Total Syntheses of Manzamine A and Related Alkaloids PowerPoint Presentation
Download Presentation
Enantioselective Total Syntheses of Manzamine A and Related Alkaloids

Loading in 2 Seconds...

  share
play fullscreen
1 / 23
Download Presentation

Enantioselective Total Syntheses of Manzamine A and Related Alkaloids - PowerPoint PPT Presentation

wiley
113 Views
Download Presentation

Enantioselective Total Syntheses of Manzamine A and Related Alkaloids

- - - - - - - - - - - - - - - - - - - - - - - - - - - E N D - - - - - - - - - - - - - - - - - - - - - - - - - - -
Presentation Transcript

  1. Enantioselective Total Syntheses of Manzamine A and Related Alkaloids John M. Humphrey, Yusheng Liao, Amjad Ali, Tobias Rein, Yue-Ling Wong, Hui-Ju Chen, Anne K. Courtney, and Stephen F. Martin* Presented by: Jixin Liu

  2. Stephen F. Martin M. June and J. Virgil Waggoner Regents Chair in Chemistry now at The University of Texas at Austin B.S. University of New Mexico (1968) Ph.D. Princeton University (1972) with Professor Edward C. Taylor Postdoctoral work at the University of Munich with Professor Rudolf Gompper, and further work with Professor George Büchi at the MIT. Known for his work in alkaloid synthesis; Current research is directed toward the syntheses of natural and unnatural products that are of biological or structural interest J. AM. CHEM. SOC. 2002, 124, 8584 8592

  3. Manzamine A, a structurally unique β-carboline alkaloid derived from marine sponge Haliclona sp., exhibiting a high level of antimalarial activity in vivo when tested in Plasmodium berghei (ANKA)-infected mice.

  4. Manzamine A

  5. 3D

  6. Manzamine A

  7. Retro synthesis

  8. Key Steps • Intramolecular Diels Alder reactions to produce the tricyclic ABC core of the manzamines • Ring-Closing Metathesis of E ring

  9. Key steps D-A reaction

  10. Key steps Ring-Closing

  11. Ring Closing

  12. Ring-Closing

  13. Forward Synthesis

  14. Forward Synthesis

  15. Forward Synthesis

  16. Forward Synthesis

  17. Forward Synthesis

  18. Forward Synthesis

  19. Pictet-Spengler

  20. Conclusion • The longest linear sequence was 21 steps • The concise approach highlights a novel strategy for assembling the tricyclic ABC ring core by a Diels Alder reaction. • 13- and 8-membered heterocyclic rings were synthesized via RCM. Thank you!