First Total Synthesis of the Bioactive Arylnaphthyl Lignan 4-O -Glycosides Phyllanthusmin D and 4′′-O -Acetylmananthoside B

Autor:	Jian-Song Sun, Hui Liu, Jian-Hui Xia, Lei Liu, De-Yong Liu, Yang Hu
Rok vydání:	2017
Předmět:	chemistry.chemical_classification Lignan Atropisomer Glycosylation 010405 organic chemistry Longest linear sequence Stereochemistry Organic Chemistry Glycoside Total synthesis 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound chemistry Physical and Theoretical Chemistry Selectivity Cytotoxicity
Zdroj:	European Journal of Organic Chemistry. 2017:3674-3680
ISSN:	1434-193X
Popis:	Based on the orchestrated application of PTC and Yu glycosylations, the first total synthesis of arylnaphthalide glycosides, phyllanthusmin D and 4''-O-acetylmananthoside B, which were claimed to be ideal antitumoral lead compounds in terms of cytotoxicity, cytotoxic selectivity, and novel working mechanism, were achieved. With easily accessible compounds as starting materials, the two target molecules were obtained in the longest linear sequence of 9 and 15 steps with 29%, 9% overall yields, respectively. Through the synthetic investigation an efficient and scalable synthetic route to diphyllin was established and the atropisomeric phenomenon in arylnaphthalide glycosides was also confirmed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c9a717261fedfbb30133cae415dd4a98 https://doi.org/10.1002/ejoc.201700556 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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