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Synthetic studies on lycopodine: construction of hexahydrojulolidine core by intramolecular Mannich reaction
Affiliation:1. Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca'' Foscari Venezia, Via Torino 155, 30172 Mestre Venezia, Italy;2. Departamento de Química Inorgánica, Universidade de Vigo, Facultade de Química, Edificio de Ciencias Experimentais, 36310 Vigo, Galicia, Spain;1. Experimental Physics Department, Ural Federal University, 19 Mira Street, Yekaterinburg 620002, Russia;2. Institute of Physics, University of Tartu, 14c Ravila Street, Tartu 50411, Estonia;1. Institute of Ecological Soil Science, M.V. Lomonosov Moscow State University, Leninskie Goru, MSU, 119992 Moscow, Russian Federation;2. Dokuchaev Soil Institute, Russian Academy of Science, Pyzhevski lane, 7, 109017 Moscow Russia;3. Eurasian Center for Food Security, M.V. Lomonosov Moscow State University, Leninskie Goru, MSU, 119992 Moscow, Russian Federation;4. Institute of Geography, Russian Academy of Sciences, Russian Federation
Abstract:The tricyclic core skeleton of lycopodine was constructed by the intramolecular Mannich reaction of a 12-membered cyclic amine. The concise assembly of the macrocyclic intermediate was executed by the sequential inter- and intramolecular N-alkylation of a linear diol using Ns-amide. The fully functionalized diol was prepared via Michael reaction of enone and malonate. The key Mannich reaction proceeded smoothly in the presence of silica gel to provide the tricyclic core skeleton of lycopodine.
Keywords:Mannich reaction  Cascade reaction  Oxidation  Lycopodine  Alkaloid
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