Enantioselective Total Syntheses of Manzamine A and Related Alkaloids John M. Humphrey, Yusheng Liao, Amjad Ali, Tobias Rein, Yue-Ling Wong, Hui-Ju Chen,

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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

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,

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.

Manzamine A

3D

Manzamine A

Retro synthesis

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

Key steps D-A reaction

Key steps Ring-Closing

Ring Closing

Ring-Closing

Forward Synthesis

Pictet-Spengler

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.