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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2020
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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. |
format | Online Article Text |
id | pubmed-9047396 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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