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Concise Total Synthesis of (+)-Lyconadin A

Concise Total Synthesis of (+)-Lyconadin A. Research by: Tohru Fukuyama Presentation by: Carl Brothers. Tohru Fukuyama. Chemistry Professor at University of Tokyo in Japan Graduate school of Pharmaceutical Sciences Synthetic Natural Products chemistry Discovered Fukuyama Coupling in 1998.

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Concise Total Synthesis of (+)-Lyconadin A

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  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 Lab Ring 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

  10. Treatment of 11 with isoamyl nitrite

  11. Michael • 8.1% overall yield by nitrosoalkene method. • 11.6% overall yield by sulfide method.

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