Synthesis of the ABC Ring of Calyciphylline A-Type Alkaloids by a Stereocontrolled Aldol Cyclization: Formal Synthesis of (±)-Himalensine A

[Image: see text] 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 throug...

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Autores principales: Marquès, Clàudia, Diaba, Faïza, Gómez-Bengoa, Enrique, Bonjoch, Josep
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9881646/
https://www.ncbi.nlm.nih.gov/pubmed/35862855
http://dx.doi.org/10.1021/acs.joc.2c01171
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author Marquès, Clàudia
Diaba, Faïza
Gómez-Bengoa, Enrique
Bonjoch, Josep
author_facet Marquès, Clàudia
Diaba, Faïza
Gómez-Bengoa, Enrique
Bonjoch, Josep
author_sort Marquès, Clàudia
collection PubMed
description [Image: see text] 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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spelling pubmed-98816462023-01-28 Synthesis of the ABC Ring of Calyciphylline A-Type Alkaloids by a Stereocontrolled Aldol Cyclization: Formal Synthesis of (±)-Himalensine A Marquès, Clàudia Diaba, Faïza Gómez-Bengoa, Enrique Bonjoch, Josep J Org Chem [Image: see text] 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. American Chemical Society 2022-07-21 /pmc/articles/PMC9881646/ /pubmed/35862855 http://dx.doi.org/10.1021/acs.joc.2c01171 Text en © 2022 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Marquès, Clàudia
Diaba, Faïza
Gómez-Bengoa, Enrique
Bonjoch, Josep
Synthesis of the ABC Ring of Calyciphylline A-Type Alkaloids by a Stereocontrolled Aldol Cyclization: Formal Synthesis of (±)-Himalensine A
title Synthesis of the ABC Ring of Calyciphylline A-Type Alkaloids by a Stereocontrolled Aldol Cyclization: Formal Synthesis of (±)-Himalensine A
title_full Synthesis of the ABC Ring of Calyciphylline A-Type Alkaloids by a Stereocontrolled Aldol Cyclization: Formal Synthesis of (±)-Himalensine A
title_fullStr Synthesis of the ABC Ring of Calyciphylline A-Type Alkaloids by a Stereocontrolled Aldol Cyclization: Formal Synthesis of (±)-Himalensine A
title_full_unstemmed Synthesis of the ABC Ring of Calyciphylline A-Type Alkaloids by a Stereocontrolled Aldol Cyclization: Formal Synthesis of (±)-Himalensine A
title_short Synthesis of the ABC Ring of Calyciphylline A-Type Alkaloids by a Stereocontrolled Aldol Cyclization: Formal Synthesis of (±)-Himalensine A
title_sort synthesis of the abc ring of calyciphylline a-type alkaloids by a stereocontrolled aldol cyclization: formal synthesis of (±)-himalensine a
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9881646/
https://www.ncbi.nlm.nih.gov/pubmed/35862855
http://dx.doi.org/10.1021/acs.joc.2c01171
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