De Novo Synthesis of Orthogonally-Protected C2-Fluoro Digitoxoses and Cymaroses: Development and Application for the Synthesis of Fluorinated Digoxin

Autor:	Ming Zhang, Hong-Wei Chen, Qing-Quan Liu, Feng-Teng Gao, Yi-Xian Li, Xiang-Guo Hu, Chu-Yi Yu
Rok vydání:	2021
Předmět:	Digoxin Halogenation Organic Chemistry Stereoisomerism Fluorine Hexoses
Zdroj:	The Journal of Organic Chemistry. 87:1272-1284
ISSN:	1520-6904 0022-3263
Popis:	Inspired by Roush's pioneering work on rare sugars, we have developed a scalable, stereoselective, de novo synthesis of orthogonally protected C2-fluoro digitoxose and cymarose, utilizing Sharpless kinetic resolution and organocatalytic fluorination as key steps. The utility of this strategy is demonstrated by the synthesis of a fluorinated analogue of digoxin, which indicates the fluorine on the sugar ring may have a significant impact on biological activity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a65dc17e819c99b6213b1dce3389dcb2 https://doi.org/10.1021/acs.joc.1c02592 Zobrazit plný text záznamu