Sintese total da (-)-aza-isoaltolactona / Total synthesis of (-)-aza-isoaltholactone

AUTOR(ES)

Marcelo Rodrigues dos Santos

DATA DE PUBLICAÇÃO

2008

RESUMO

Natural products are a rich source of medicinal compounds, and have also inspired the design of non-natural product of relevant pharmaceutical importance. The structure-activity relationship in natural product are an interesting area for research. In this work, we describe the synthesis of (-)-aza-isoaltholactone, an analogous of the (-)-isoaltolactone. The synthetical strategy, uses a Heck arylation reaction was the key step, involving the coupling the benzenediazonium tetrafluorborate salt with an electron rich endocyclic enecarbamate. The endocyclic enecarbamate was eficiently obtained fron L-pyroglutamic acid in four steps, with 58% overall yield. The Heck reaction showed dependence on the olefin electronic characteristics as well as on the arenediazonium salt. This dependence is also reflected on the observed selectivity. In this work, the first total synthesis of (-)-aza-isoaltholactone was accomplished in 13 steps with 7% overall yield from L-pyroglutamic acid.

ASSUNTO(S)

heck reaction dizonium salts sais de diazonio styryllactones estiril lactonas reação de heck

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