RT journal article
T1 Enantioselective Total Syntheses of (R)- and (S)-Naphthotectone, and Stereochemical Assignment of the Natural Product
A1 Guerrero-Vásquez, Guillermo A.
A1 D. Galarza, Flávia A.
A1 Kleber Z. Andrade, Carlos
A1 González Molinillo, José María
A1 Macías Domínguez, Francisco Antonio
A2 Química Orgánica
K1 total synthesis
K1 natural products
K1 fused ring systems
K1 quinones
K1 configuration determination
K1 electrochemistry
AB 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 %.
PB European Journal of Organic Chemistry
YR 2016
FD 2016-02
LK http://hdl.handle.net/10498/20327
UL http://hdl.handle.net/10498/20327
LA eng
DS Repositorio Institucional de la Universidad de Cádiz
RD 12-nov-2026