by#rob#panish# - university of delaware...lycopodium#alkaloids# • potentinhibitors#of#...
TRANSCRIPT
By Rob Panish
• Yang, Y.; Shen, L.; Huang, J.; Wei, K. J. Org. Chem. 2011, XX, XXXX.
Lycopodium Alkaloids • Potent inhibitors of acetylcholinesterase • Neurotrophic acFvity • AnFcancer properFes • FawceJmine first isolated in 1959 by Burnell
– First synthesis in 1979 by Inubushi • Lycoflexine first isolated in 1973 by Ayer • 8-‐DeoxyserraFnine first synthesis in 1979 by Inubushi
Retrosynthesis
Helquist AnnulaFon
• Bal, S.A.; Marfat, A.; Helquist, P. J. Org. Chem. 1982, 47, 5045-‐50.
Synthesis
• Helquist AnnulaFon: cis 6/5 bicycle synthesis
• Of common aza tricycle intermediate 8 Synthesis
Synthesis • Of (-‐)-‐8-‐deoxyserraFnine (7)
Synthesis • Abempts at lycojapodine A (5)
Synthesis • Of (+)-‐fawceJmine (1)
Synthesis • Of (+)-‐lycoflexine (4)