Premium
Highly Functionalized and Potent Antiviral Cyclopentane Derivatives Formed by a Tandem Process Consisting of Organometallic, Transition‐Metal‐Catalyzed, and Radical Reaction Steps
Author(s) -
Jagtap Pratap R.,
Ford Leigh,
Deister Elmar,
Pohl Radek,
Císařová Ivana,
Hodek Jan,
Weber Jan,
Mackman Richard,
Bahador Gina,
Jahn Ullrich
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402595
Subject(s) - cyclopentane , chemistry , allylic rearrangement , catalysis , combinatorial chemistry , group 2 organometallic chemistry , isomerization , tandem , photochemistry , organic chemistry , molecule , materials science , composite material
A simple modular tandem approach to multiply substituted cyclopentane derivatives is reported, which succeeds by joining organometallic addition, conjugate addition, radical cyclization, and oxygenation steps. The key steps enabling this tandem process are the thus far rarely used isomerization of allylic alkoxides to enolates and single‐electron transfer to merge the organometallic step with the radical and oxygenation chemistry. This controlled lineup of multiple electronically contrasting reactive intermediates provides versatile access to highly functionalized cyclopentane derivatives from very simple and readily available commodity precursors. The antiviral activity of the synthesized compounds was screened and a number of compounds showed potent activity against hepatitis C and dengue viruses.