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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/216055
Synthesis of the ABC ring of calyciphylline A-type alkaloids by a stereocontrolled aldol cyclization: Formal synthesis of (±)-Himalensine A
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A synthetic approach to a functionalized ABC-tricyclic framework of calyciphilline A-type alkaloids, a building block toward this class of alkaloids, is reported. The key synthetic steps involve a radical cyclization to form the hydroindole system and piperidine ring closure through a stereocontrolled aldol cyclization. The resulting alcohol allows the methyl group to be installed in the bowl-shaped azatricyclic structure; this crucial reaction takes place with configuration retention. The synthesis of azatricyclic compound I constitutes a formal synthesis of himalensine A.
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MARQUÈS, Clàudia, et al. Synthesis of the ABC ring of calyciphylline A-type alkaloids by a stereocontrolled aldol cyclization: Formal synthesis of (±)-Himalensine A. Journal of Organic Chemistry. 2022. Vol. 87, num. 15, pags. 10516-10522. ISSN 0022-3263. [consulted: 6 of June of 2026]. Available at: https://hdl.handle.net/2445/216055