Síntese total dos ácidos pterídicos A e B / Total synthesis of pteridic acids A and B

AUTOR(ES)

Airton Gonçalves Salles Junior

FONTE

IBICT - Instituto Brasileiro de Informação em Ciência e Tecnologia

DATA DE PUBLICAÇÃO

04/12/2009

RESUMO

This work describes the convergent stereoselective synthesis of pteridic acids A and B. Our strategy involved a lithium enolate-mediated aldol reaction between ethyl ketone 5 and aldehyde 4 as the key step to set up C5-C15 fragment favoring 1,2-syn anti-Felkin adduct. As far we know, this is the first example of an aldol reaction between a chiral enolate of a (Z) enone and a chiral aldehyde. Efficient spiroketalization followed by additional transformations provided pteridic acids A and B in 2.9% and 2.8% overall yields, respectively. This approach compares very well with previously published routes and attracts attention to the novel and interesting C9-C10 bond construction to obtain C5-C15 fragment.

ASSUNTO(S)

antitumoral enolatos de litio estereoindução dupla espirocetais anti-tumoral lithium enolates double stereoinduction spiroketals

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