Eugenio Hernández-Fernández

Asymmetric alkylation of dimethoxyphosphoryl-N-[1-(S)-α-methylbenzyl]acetamide enolates. Synthesis of both stereoisomers from the same source of chirality by changing the equivalents of LDA

A new methodology has been developed for the synthesis of both stereoisomers from a single chiral source.

Synthesis, antimycobacterial and cytotoxic activity of α,β-unsaturated amides and 2,4-disubstituted oxazoline derivatives.

The synthesis of six α,β,-unsaturated amides and six 2,4-disubstituted oxazolines derivatives and their evaluation against two Mycobacterium tuberculosis strains (sensitive H37Rv and a resistant clinical isolate) is reported. 2,4-Disubstituted oxazolines (S)-3b,d,e were the most active in the sensitive strain with a MIC of 14.2, 13.6 and 10.8μM, respectively, and the compounds (S)-3d,f were the most active against resistant strain with a MIC of 6.8 and 7.4μM. The ex-vivo evaluation of hepatotoxicity on precision-cut rat liver slices was also tested for the α,β-unsaturated amides (S)-2b and (S)-2d,f and for the oxazolines (S)-3b and (S)-3d,f at different concentrations (5, 15 and 30μg/mL). The results indicate that these compounds possess promising antimycobacterial activity and at the same time are not hepatotoxic. These findings open the possibility for development of new drugs against tuberculosis.

Synthesis of novel tetrahydroindeno[1,2-b]pyrrolidines via Ugi multicomponent and palladium-catalyzed aerobic oxidative cyclization

ABSTRACT Novel tetrahydroindeno[1,2-b]pyrrolidines were conveniently prepared in moderate to good yields via a sequential Ugi multicomponent reaction or Staudinger/aza-Wittig/Ugi combination, followed by the palladium-catalyzed aerobic oxidative cyclization of the resulting Ugi adducts. GRAPHICAL ABSTRACT

Practical and efficient synthesis of (E)-α,β-unsaturated amides bearing (S)-α-methylbenzylamine from 2-phosphonamides via Horner-Wadsworth-Emmons reaction

The highly stereoselective synthesis of (E)-α,β-unsaturated amides bearing (S)-a-methylbenzylamine was achieved from 2-phosphonamides via Homer-Wadsworth-Emmons reaction. The starting phosphonamides are easily prepared in two steps with excellent yields via the standard Arbuzov reaction of trimethylphosphite and α-bromoamides.