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By Rob Panish
• Yang, Y.; Shen, L.; Huang, J.; Wei, K. J. Org. Chem. 2011, XX, XXXX.
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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
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Retrosynthesis
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Helquist AnnulaFon
• Bal, S.A.; Marfat, A.; Helquist, P. J. Org. Chem. 1982, 47, 5045-‐50.
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Synthesis
• Helquist AnnulaFon: cis 6/5 bicycle synthesis
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• Of common aza tricycle intermediate 8 Synthesis
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Synthesis • Of (-‐)-‐8-‐deoxyserraFnine (7)
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Synthesis • Abempts at lycojapodine A (5)
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Synthesis • Of (+)-‐fawceJmine (1)
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Synthesis • Of (+)-‐lycoflexine (4)