Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs

Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquino...

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Detalles Bibliográficos
Autores principales: Zheng, Bo, Qu, Hui-Ya, Meng, Tian-Zhuo, Lu, Xia, Zheng, Jie, He, Yun-Gang, Fan, Qi-Qi, Shi, Xiao-Xin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9084380/
https://www.ncbi.nlm.nih.gov/pubmed/35548004
http://dx.doi.org/10.1039/c8ra05338c
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author Zheng, Bo
Qu, Hui-Ya
Meng, Tian-Zhuo
Lu, Xia
Zheng, Jie
He, Yun-Gang
Fan, Qi-Qi
Shi, Xiao-Xin
author_facet Zheng, Bo
Qu, Hui-Ya
Meng, Tian-Zhuo
Lu, Xia
Zheng, Jie
He, Yun-Gang
Fan, Qi-Qi
Shi, Xiao-Xin
author_sort Zheng, Bo
collection PubMed
description Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.
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spelling pubmed-90843802022-05-10 Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs Zheng, Bo Qu, Hui-Ya Meng, Tian-Zhuo Lu, Xia Zheng, Jie He, Yun-Gang Fan, Qi-Qi Shi, Xiao-Xin RSC Adv Chemistry Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core. The Royal Society of Chemistry 2018-08-14 /pmc/articles/PMC9084380/ /pubmed/35548004 http://dx.doi.org/10.1039/c8ra05338c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Zheng, Bo
Qu, Hui-Ya
Meng, Tian-Zhuo
Lu, Xia
Zheng, Jie
He, Yun-Gang
Fan, Qi-Qi
Shi, Xiao-Xin
Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs
title Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs
title_full Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs
title_fullStr Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs
title_full_unstemmed Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs
title_short Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs
title_sort novel total syntheses of oxoaporphine alkaloids enabled by mild cu-catalyzed tandem oxidation/aromatization of 1-bn-dhiqs
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9084380/
https://www.ncbi.nlm.nih.gov/pubmed/35548004
http://dx.doi.org/10.1039/c8ra05338c
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