@misc{10498/20327,
year = {2016},
month = {2},
url = {http://hdl.handle.net/10498/20327},
abstract = {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 %.},
publisher = {European Journal of Organic Chemistry},
keywords = {total synthesis},
keywords = {natural products},
keywords = {fused ring systems},
keywords = {quinones},
keywords = {configuration determination},
keywords = {electrochemistry},
title = {Enantioselective Total Syntheses of (R)- and (S)-Naphthotectone, and Stereochemical Assignment of the Natural Product},
doi = {10.1002/ejoc.201501479},
author = {Guerrero-Vásquez, Guillermo A. and D. Galarza, Flávia A. and Kleber Z. Andrade, Carlos and González Molinillo, José María and Macías Domínguez, Francisco Antonio},
}