1. Concise Total Synthesis of (+)-Lyconadin A Research by: Tohru Fukuyama Presentation by: Carl Brothers

2. Tohru Fukuyama Chemistry Professor at University of Tokyo in Japan –Graduate school of Pharmaceutical Sciences –Synthetic Natural Products chemistry Discovered Fukuyama Coupling in 1998

3. Fukuyama Coupling Coupling between a thioester and an organozinc halide in the presence of a palladium catalyst. –Mild reaction conditions –High chemoselectivity –Less toxic reagents –Stops at ketone

4. (+)-Lyconadin A –Cytotoxic to murine lymphoma L1210 cells and KB cells. –Enhances mRNA expression for nerve growth factor in astrocytoma cells. –Found in Lycopodium complanatum.

5. Lycopodium complanatum (AKA. Northern Ground Cedar) Club Moss family Ground level creeping evergreen found in acidic soils of wooded areas and rocky slopes in North America and Europe. Previously used to make a medicinal tea which would increase urine production, stimulate menstrual flow, and relieve spasms.

6. Retrosynthetic Analysis LabRing expansion D-A

7. Forward Synthesis DA Reductive amin

8. aza -prins Dibromo cyclo prop Ring expansion

9. Treatment of 11 with diphenyl disulfide Vinylogous pummer

11. Treatment of 11 with isoamyl nitrite

12. 8.1% overall yield by nitrosoalkene method. 11.6% overall yield by sulfide method. Michael