Heck arylation reaction with arenediazonium salts : applications in the total synthesis of polyhydroxylated prolines and pyrrolidines, rolipram and baclofen analogues, and in the formal synthesis of prepolycitrin A and polycitrin A / Reação de arilação de Heck com sais de arenodiazonio : aplicações nas sinteses totais de prolinas e pirrolidinas poliidroxiladas, rolipram e analogos do baclofeno, e na sintese formal de prepolicitrina A e policitrina A

AUTOR(ES)
DATA DE PUBLICAÇÃO

2008

RESUMO

The Heck-Matsuda arylation reaction is a valuable and extremely versatile synthetic procedure for carbon-carbon bond formation, based on the coupling of an olefin with an arenediazonium salt in the presence of a zerovalent palladium organometallic specie. Recently, the use of this reaction has been gaining space in total syntheses, demonstrating its viability. In this work, we presented the development of new and flexible methodologies for the efficient synthesis of several natural and synthetic products with important pharmacologic properties, using the Heck-Matsuda arylation reaction as a key stage. Totally, a set of 21 final compounds were synthesized, including: racemic and chiral polyhydroxylated prolines and pyrrolidines, Radicamine B and other chiral C-aryl-iminocyclitols analogues of Radicamines A and B, Rolipram and b-aryl-g-aminobutyric acids analogues of Baclofen, and a key precursor of Prepolycitrin A and Polycitrin A. The synthesized compounds, as well as their respective reaction intermediates, were entirely characterized and the obtained results were compared with those reported in the literature when applicable. Satisfactory analytical and spectral data were obtained in all cases.

ASSUNTO(S)

arenediazonium salts polyhydroxylated prolines sais de arenodizonio iminociclitois iminocyclitols heck prolinas poliidroxiladas

ACESSO AO ARTIGO

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