Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes

Catalan, LE; Marin, KC; Villegas, AM; Altamirano, HC; Garcia, JV; Fritis, MC

Abstract

The synthesis and structural determination of two new diterpenylhydroquinones: 2ß-acetoxy-15-phenyl-(22,25-dihydroxy)-ent-labda- 8(17),13(£)-diene (1) and 2ß-hydroxy- 15-phenyl-(22,25-dihydroxy)- ent-labda-8(17),13(E)-diene is reported (2). These compounds were obtained by coupling via Electrophilic Aromatic Substitution (EAS) of 1,4-hydroquinone with primary or tertiary allyl alcohol derivatives of the natural ent- labdanes 3 and 4. With this new method, the best results were observed when mixtures of the primary alcohol derivatives 5-6 (26% yield of compound 1) and diol derivatives 9-10 (28% yield of compound 2) were used.

Más información

Título según WOS: Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes
Título según SCOPUS: Synthesis of two new hemisynthetic diterpenylhydroquinones from natural iiwf-Labdanes
Título de la Revista: MOLECULES
Volumen: 14
Número: 6
Editorial: MDPI
Fecha de publicación: 2009
Página de inicio: 2181
Página final: 2194
Idioma: English
URL: http://www.mdpi.com/1420-3049/14/6/2181/
DOI:

10.3390/molecules14062181

Notas: ISI, SCOPUS