Synthesis of the ABC ring of calyciphylline A-type alkaloids by a stereocontrolled aldol cyclization: Formal synthesis of (±)-Himalensine A

Marquès, ClàudiaDiaba, FaïzaGómez-Bengoa, EnriqueBonjoch, Josep2024-10-252024-10-252022-07-210022-3263https://hdl.handle.net/2445/216055A 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.7 p.application/pdfengcc-by (c) Marquès et al., 2022http://creativecommons.org/licenses/by/3.0/es/Reacció aldòlicaCromatografiaMesclesAldol reactionChromatographyMixturesSynthesis of the ABC ring of calyciphylline A-type alkaloids by a stereocontrolled aldol cyclization: Formal synthesis of (±)-Himalensine Ainfo:eu-repo/semantics/article7244692024-10-25info:eu-repo/semantics/openAccess