A straightforward trifluoromethylation at the C6 position of morphinane alkaloids, their modification and evaluation of inhibition of the SARS-CoV-2 main protease

• Published in: Journal of fluorine chemistry Vol. 271; pp. 110189 - 110198
• Main Authors: Finke, Anastasija O., Krasnov, Vyacheslav I., Rybalova, Tatyana V., Chirkova, Varvara Yu, Belenkaya, Svetlana V., Volosnikova, Ekaterina A., Shcherbakov, Dmitry N., Shults, Elvira E.
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.10.2023; Elsevier
• Subjects: Carbonylation-cross-coupling reaction; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Hydroxycodeinone; Main viral protease 3CLpro; Physical Sciences; Ruppert–Prakash reagent; SARS-CoV-2; Science & Technology; Sinomenine; Trifluoromethylation; SARS-CoV-2; Trifluoromethylation; Main viral protease 3CLpro; Hydroxycodeinone; Ruppert–Prakash reagent; Carbonylation-cross-coupling reaction; Sinomenine; SUBSTITUTION; Ruppert-Prakash reagent; TRIFLUOROMETHYLTRIMETHYLSILANE; OPIOIDS; SINOMENINE DERIVATIVES; AGONIST

•A methodology for trifluoromethylation of stereoisomeric 6-ketomorphinans using Ruppert–Prakash reagent.•Selective synthesis of (9α,13α,14α)-8β‑chloro-6,7-didehydro-6-(trifluoromethyl)-3,4,7-trimethoxy-N-methylmorphinane.•(9α,13α,14α)-7,8-Didehydro-1-iodo-6α-(trifluoromethyl)-6β-(hydroxy)-3,4,7-tri...