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Synthesis And Reactivity Of Pelletierine-derived Building Blocks And Pelletierine Analogs

Lok-Hang Yan, Flore Dagorn, E. Gravel, B. Séon-Méniel, E. Poupon
Published 2012 · Chemistry

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Lycopodium alkaloids are unique (and often impressive in terms of structures) polycyclic alkaloids that attract great interest from a biological point of view and that also provide ideal targets for total synthesis. Propylpiperidine units closely related to pelletierine are involved in the biosynthesis of these alkaloids. Therefore, stable pelletierine-like compounds, especially a (R)-phenylglycinol-based oxazolopiperidine analog, were prepared and their reactivity investigated. The compounds described in this work expand the tool-box of small building blocks in the piperidine series and pelletierine analogs and could be suitable for the synthesis of Lycopodium alkaloids following biosynthetically inspired strategies.
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