Marta Feroci

Synthesis of chiral oxazolidin-2-ones by 1,2-amino alcohols, carbon dioxide and electrogenerated acetonitrile anion

An improved electrochemical synthesis of chiral oxazolidin-2-ones from chiral 1,2-amino alcohols is obtained by direct electrolysis of solutions of MeCN–TEAP containing the amino alcohol, with subsequent CO2 bubbling and addition of TsCl. This synthesis avoids any addition of bases or probases and yields oxazolidinones in high yields.

The reaction of amines with an electrogenerated base. Improved synthesis of arylcarbamic esters

Abstract The electrogenerated base of 2-pyrrolidone reacts with amines and anilines yielding the corresponding alkyl and aryl carbamates, after addition of carbon dioxide and ethyl iodide. Arylcarbamic esters are obtained in very good yields under mild reaction conditions with respect to the methods so far reported.

The system as mild and safe carboxylating reagent synthesis of organic carbonates

Abstract The system, originating from electrochemical one-electron reduction of dioxygen in dipolar aprotic solvents and in the presence of CO 2 , converts primary and secondary alcohols bearing a leaving group at α orβ position into the corresponding cyclic carbonates in high to excellent yields. Unsubstituted alcohols are also converted, but in unsatisfactory yields, into the corresponding alkyl ethyl carbonates after completion of the reaction by addition of Etl. Tertiary alcohols and phenols are stable to the reagent, thus allowing selective carboxylation of polyhydroxy derivatives. CH-acid containing compounds underfo diferent reactions, if any, with the reagent but in the cases under study the formation of carboxylation products has never been observed.

Isopropenyl acetate, a remarkable, cheap and acylating agent of amines under solvent- and catalyst-free conditions: a systematic investigation

Isopropenyl acetate was proved to be an efficient reagent for acetylation of amine in the absence of solvent and catalyst. The corresponding acetamides were obtained in very high yields without any purification.

Electrochemically induced Knoevenagel condensation in solvent- and supporting electrolyte-free conditions

Solvent- and supporting electrolyte-free electrochemically induced Knoevenagel condensation of malononitrile with aldehydes or ketones, at 40 °C, yields ylidenemalononitriles in high yields.

Palladium-catalyzed electrochemical carbonylation of 2-amino-1-alkanols to oxazolidin-2-ones under very mild conditions

Abstract A new procedure for an efficient synthesis of oxazolidin-2-ones was developed. 2-Amino-1-alkanols undergo oxidative carbonylation under atmospheric pressure of carbon monoxide at room temperature using Pd(II) catalyst in combination with its anodic recycling at a graphite electrode.

New synthesis of oxazolidin-2-ones

Abstract Electrochemically generated tetraethylammonium peroxydicarbonate (TEAPC) and tetraethylammonium carbonate (TEAC) react under very mild conditions, with 1,2-amino alcohols affording, after addition of tosyl chloride, the corresponding oxazolidin-2-ones in fair to good yields.

Electrochemically-initiated Michael addition of chiral acetoacetic derivatives to methyl vinyl ketone: stereocontrolled construction of quaternary carbon centers

Abstract Stereoselective conjugate addition of chiral β-dicarbonyl derivatives to methyl vinyl ketone was promoted by electrolysis, using a catalytic amount of electricity. With respect to the metal-catalyzed methods, the electrochemical, metal-free conditions resulted in enhanced reactivity of the electrogenerated enolates, so that the Michael addition was found to occur under mild conditions and short reaction times, affording products with significant diastereoisomeric excesses. When Oppolzers sultam was used as the chiral inductor and prolonged reaction times were employed, a reversal in the stereoselectivity was observed, evidencing kinetic control in the electrochemically-induced addition and subsequent thermodynamic equilibration. The electrochemically-based method was also exploited for the elaboration of quaternary stereogenic carbon centers.

Electrochemical generation of chiral oxazolidin-2-ones anions: a new procedure for the highly diastereoselective conjugate addition to nitroalkenes

Abstract A mild and efficient electrochemical alternative to classical base-catalyzed conjugate addition of nitrogen nucleophiles is reported here. The cleavage of the carbamic NH bond of Evans’ chiral auxiliaries can be very efficiently performed by electrolysis under galvanostatic control and the resulting naked anions used for highly diastereoselective conjugate addition to nitroalkenes. The degree of stereoselectivity was shown to depend on the steric hindrance of the group at the ring C(4) of the starting oxazolidin-2-one.

CACHEXIA: NOVEL PERSPECTIVES FOR AN OLD SYNDROME

Cachexia, literally “bad condition”, a syndrome reported even in the Old Testament, is associated to a variety of chronic diseases and to several kinds of traumatic injuries. Although an official definition of cachexia is still missing, this multi systemic syndrome is characterized by a massive loss of skeletal muscle and fat tissue. Such an important loss of body mass is often a direct cause of death, interferes with therapies and always represents a poor prognostic factor. In sharp contrast with the management of chronic disease states, a cure for cachexia is still missing. In recent years striking discoveries have cast light upon the molecular mechanisms underlying cachexia. Muscle specific targets for pharmacological, gene or cell therapy approaches have been identified and are summarized in this review. Although limited to cancer cachexia, the first phase I-III clinical trials have been recently terminated or are ongoing. These efforts are opening the possibility to prevent cachexia or treat it with novel approaches in the near future.