Cristina Sousa

REQUIMTE · Faculdade de Ciências da Universidade do Porto

Iminosugars continue receiving a great deal of attention from chemists and biochemists for their potential as pharmaceutics. This is a comprehensive review of the methods found in the literature for the synthesis of piperidine, pyrrolidine, indolizidine, and pirrolizidine iminosugars, starting from D/L-erythrose and D/L-threose carbon chains (tetro...

The appearance and quick spread of the new severe acute respiratory syndrome coronavirus disease, COVID-19, brought major societal challenges. Importantly, suitable medical diagnosis procedures and smooth clinical management of the disease are an emergent need, which must be anchored on novel diagnostic methods and devices. Novel molecular diagnost...

A new D-erythrose 1,3-dioxane derivative was synthetized from D-glucose and found to be a highly stereo-selective template as dipolarophile. Different 1,3-dipoles of allenyl-type were employed, giving different regio-selectivities, depending on its nature; the regio-selectivity is complete with alkyl azides and phenyldiazomethane, but is inexistent...

Given the pandemic situation, there is an urgent need for an accurate test to monitor antibodies anti-SARS-CoV-2, providing crucial epidemiological and clinical information to monitor the evolution of coronavirus disease in 2019 (COVID-19) and to stratify the immunized and asymptomatic population. Therefore, this paper describes a new cellulose-bas...

A five-step synthesis of (S)-7-hydroxy-8a-epi-5-aza-swainsonine was accessed in good overall yield from readily available D-erythrosyl benzylidene acetal 1,3-butadiene. The key step of the reaction sequence is a full stereoselective Diels-Alder cycloaddition between the diene and dienophile: diethyl azodicarboxylate (DEAD)/ di- t-butyl azodicarboxy...

d-Erythrosyl aziridines were obtained from d-erythrosyl triazoles either by photolysis or through diazirine intermediates. These were found to undergo rich, high yielding chemistry by reaction with protic acids (HCl, BiI3/H2O and trifluoroacetic acid) leading to two types of furanoid sugar α-amino acids, and polyhydroxylprolines. Based on experimen...

This is the first synthetic report of (3S,4R)-dihydroxy-N-alkyl-L-homoprolines described so far. 2,4-O-Benzylidene-D-erythrose was obtained from D-glucose with an improved yield, and then transformed into the title (3S,4R)-dihydroxy-N-alkyl-L-homoprolines, in a two-step strategy, with excellent overall yields. Hydrogenolysis of the benzyl group led...

The synthesis of a 1,5-lactone 2,4-O-alkylidene-D-erythrose derivative was found to be a highly stereoselective template in Michael addition trough the reaction of a D-erythrosyl 1,5-lactone derivative with nitrogen and sulfur nucleophiles. The sulfur adducts formed are 1 (D-erythrose derivative):1 (nucleophile), and the nitrogen adducts are 1:2. B...

Maleimides were combined with D-erythrose benzylidene-acetal 1,3-butadienes to study the facial selectivity of the Diels-Alder cycloadditions. The selectivity was found to range from moderate to good. The reaction diastereotopicity can be reversed with the temperature. Simultaneous coordination of the diene, having a free hydroxy group, and maleimi...

This comprehensive review deals with the synthesis of 1-azafagomine, analogues, and derivatives having the Diels-Alder cycloaddition as the key step. Most of the compounds referred are racemic or have been resolved by lipase transesterification. There are two asymmetric cycloadditions leading to 1-azafagomine or to an analogue. In one case both ena...

5-(5-Aminoimidazol-4-yl)-1,2,4-triazol-3-ones were obtained under mild experimental conditions from 5-amino-4-(N-ethoxycarbonyl) cyanoformimidoyl imidazoles and hydrazine in a rapid one-pot reaction. When hydroxylamine hydrochloride was used, in the presence of base, the corresponding 1,2,4-oxadiazol-5ones were isolated. An equally fast reaction oc...