Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties

Herein, we report the total synthesis of landomycins Q and R as well as the aglycone core, namely anhydrolandomycinone and a related core analogue. The synthesis features an acetate-assisted arylation method for construction of the hindered B-ring in the core component and a one-pot aromatization–de...

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Autores principales: Lai, Yao-Hsuan, Mondal, Soumik, Su, Hsin-Tzu, Huang, Sheng-Cih, Wu, Mine-Hsine, Huang, I.-Wen, Yang Lauderdale, Tsai-Ling, Song, Jen-Shin, Shia, Kak-Shan, Mong, Kwok-Kong Tony
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8695357/
https://www.ncbi.nlm.nih.gov/pubmed/35423459
http://dx.doi.org/10.1039/d1ra01088c
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author Lai, Yao-Hsuan
Mondal, Soumik
Su, Hsin-Tzu
Huang, Sheng-Cih
Wu, Mine-Hsine
Huang, I.-Wen
Yang Lauderdale, Tsai-Ling
Song, Jen-Shin
Shia, Kak-Shan
Mong, Kwok-Kong Tony
author_facet Lai, Yao-Hsuan
Mondal, Soumik
Su, Hsin-Tzu
Huang, Sheng-Cih
Wu, Mine-Hsine
Huang, I.-Wen
Yang Lauderdale, Tsai-Ling
Song, Jen-Shin
Shia, Kak-Shan
Mong, Kwok-Kong Tony
author_sort Lai, Yao-Hsuan
collection PubMed
description Herein, we report the total synthesis of landomycins Q and R as well as the aglycone core, namely anhydrolandomycinone and a related core analogue. The synthesis features an acetate-assisted arylation method for construction of the hindered B-ring in the core component and a one-pot aromatization–deiodination–denbenzylation procedure to streamline the global functional and protecting group manuipulation. Subsequent cytotoxicity and antibacterial studies revealed that the landomycin R is a potential antibacterial agent against methicillin-resistant Staphylococcus aureus.
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spelling pubmed-86953572022-04-13 Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties Lai, Yao-Hsuan Mondal, Soumik Su, Hsin-Tzu Huang, Sheng-Cih Wu, Mine-Hsine Huang, I.-Wen Yang Lauderdale, Tsai-Ling Song, Jen-Shin Shia, Kak-Shan Mong, Kwok-Kong Tony RSC Adv Chemistry Herein, we report the total synthesis of landomycins Q and R as well as the aglycone core, namely anhydrolandomycinone and a related core analogue. The synthesis features an acetate-assisted arylation method for construction of the hindered B-ring in the core component and a one-pot aromatization–deiodination–denbenzylation procedure to streamline the global functional and protecting group manuipulation. Subsequent cytotoxicity and antibacterial studies revealed that the landomycin R is a potential antibacterial agent against methicillin-resistant Staphylococcus aureus. The Royal Society of Chemistry 2021-03-02 /pmc/articles/PMC8695357/ /pubmed/35423459 http://dx.doi.org/10.1039/d1ra01088c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Lai, Yao-Hsuan
Mondal, Soumik
Su, Hsin-Tzu
Huang, Sheng-Cih
Wu, Mine-Hsine
Huang, I.-Wen
Yang Lauderdale, Tsai-Ling
Song, Jen-Shin
Shia, Kak-Shan
Mong, Kwok-Kong Tony
Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties
title Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties
title_full Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties
title_fullStr Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties
title_full_unstemmed Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties
title_short Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties
title_sort total synthesis of landomycins q and r and related core structures for exploration of the cytotoxicity and antibacterial properties
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8695357/
https://www.ncbi.nlm.nih.gov/pubmed/35423459
http://dx.doi.org/10.1039/d1ra01088c
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