%0 Journal Article 
%A Guerrero-Vásquez, Guillermo A.
%A D. Galarza, Flávia A.
%A Kleber Z. Andrade, Carlos
%A González Molinillo, José María
%A Macías Domínguez, Francisco Antonio
%T Enantioselective Total Syntheses of (R)- and (S)-Naphthotectone, and Stereochemical Assignment of the Natural Product
%D 2016
%U http://hdl.handle.net/10498/20327
%X Both isomers of naphthotectone, an isoprenoid quinone from Verbenaceae Tectona grandis possessing interesting biological activities, were enantioselectively obtained by two different synthetic routes in which the carbon side-chain of the naphthoquinone core was introduced using either a Sonogashira or a Heck coupling reaction. In both cases, the naphthoquinone core of the final products was obtained by a late-stage anodic treatment. (R)-Naphthotectone was obtained in six steps from leuconaphthazarin with an overall yield of 38 % and an enantiomeric excess of 86 %. This compound was found to have the same absolute configuration as the natural product at its C-3′ stereogenic center. (S)-Naphthotectone was obtained in five steps from leuconaphthazarin with an overall yield of 36 %
and an enantiomeric excess of 80 %.
%K total synthesis
%K natural products
%K fused ring systems
%K quinones
%K configuration determination
%K electrochemistry
%~ Universidad de Cádiz