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Total synthesis of Palmarumycin BGs, C(1) and Guignardin E

The first total synthesis of Palmarumycin BG1–3, BG5–6, C(1) and Guignardin E (1–7) were achieved by the same intermediate Palmarumycin C(2) through a N-benzyl cinchoninium chloride-catalyzed epoxidation, an organoselenium-mediated reduction, and a cerium(iii) chloride hydrate-promoted regioselectiv...

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Autores principales: Liu, Xinlei, Li, Shuyi, Wei, Xinyu, Zhao, Yu, Lai, Daowan, Zhou, Ligang, Wang, Mingan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9047396/
https://www.ncbi.nlm.nih.gov/pubmed/35494718
http://dx.doi.org/10.1039/c9ra10316c
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author Liu, Xinlei
Li, Shuyi
Wei, Xinyu
Zhao, Yu
Lai, Daowan
Zhou, Ligang
Wang, Mingan
author_facet Liu, Xinlei
Li, Shuyi
Wei, Xinyu
Zhao, Yu
Lai, Daowan
Zhou, Ligang
Wang, Mingan
author_sort Liu, Xinlei
collection PubMed
description The first total synthesis of Palmarumycin BG1–3, BG5–6, C(1) and Guignardin E (1–7) were achieved by the same intermediate Palmarumycin C(2) through a N-benzyl cinchoninium chloride-catalyzed epoxidation, an organoselenium-mediated reduction, and a cerium(iii) chloride hydrate-promoted regioselective ring-opening and elimination of cyclic α,β-epoxy ketone as the key steps via6–7 step routes using 1,8-dihydroxynaphthalene (DHN) and 5-methoxytetralone as the starting materials in overall yields of 1.0–17.4%, respectively. Their structures and absolute configurations were characterized and determined by (1)H, (13)C NMR, IR, HR-ESI-MS and X-ray diffraction data. These compounds displayed significant inhibition activities against HCT116, U87-MG, HepG2, BGC823 and PC9 cell lines.
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spelling pubmed-90473962022-04-28 Total synthesis of Palmarumycin BGs, C(1) and Guignardin E Liu, Xinlei Li, Shuyi Wei, Xinyu Zhao, Yu Lai, Daowan Zhou, Ligang Wang, Mingan RSC Adv Chemistry The first total synthesis of Palmarumycin BG1–3, BG5–6, C(1) and Guignardin E (1–7) were achieved by the same intermediate Palmarumycin C(2) through a N-benzyl cinchoninium chloride-catalyzed epoxidation, an organoselenium-mediated reduction, and a cerium(iii) chloride hydrate-promoted regioselective ring-opening and elimination of cyclic α,β-epoxy ketone as the key steps via6–7 step routes using 1,8-dihydroxynaphthalene (DHN) and 5-methoxytetralone as the starting materials in overall yields of 1.0–17.4%, respectively. Their structures and absolute configurations were characterized and determined by (1)H, (13)C NMR, IR, HR-ESI-MS and X-ray diffraction data. These compounds displayed significant inhibition activities against HCT116, U87-MG, HepG2, BGC823 and PC9 cell lines. The Royal Society of Chemistry 2020-01-08 /pmc/articles/PMC9047396/ /pubmed/35494718 http://dx.doi.org/10.1039/c9ra10316c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Liu, Xinlei
Li, Shuyi
Wei, Xinyu
Zhao, Yu
Lai, Daowan
Zhou, Ligang
Wang, Mingan
Total synthesis of Palmarumycin BGs, C(1) and Guignardin E
title Total synthesis of Palmarumycin BGs, C(1) and Guignardin E
title_full Total synthesis of Palmarumycin BGs, C(1) and Guignardin E
title_fullStr Total synthesis of Palmarumycin BGs, C(1) and Guignardin E
title_full_unstemmed Total synthesis of Palmarumycin BGs, C(1) and Guignardin E
title_short Total synthesis of Palmarumycin BGs, C(1) and Guignardin E
title_sort total synthesis of palmarumycin bgs, c(1) and guignardin e
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9047396/
https://www.ncbi.nlm.nih.gov/pubmed/35494718
http://dx.doi.org/10.1039/c9ra10316c
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