RESUMEN
[reaction: see text] A new route toward puupehenone-related bioactive metabolites from (-)-sclareol, based on the palladium(II)-mediated diastereoselective cyclization of a drimenylphenol, is described. Utilizing this, the first enantiospecific synthesis of the antitumor and antimalarial (-)-15-oxopuupehenol, together with improved syntheses of (+)-puupehenone, (+)-puupehedione, and (+)-15-cyanopuupehenone, were accomplished.
Asunto(s)
Antimaláricos/síntesis química , Antineoplásicos/síntesis química , Diterpenos/química , Diterpenos/síntesis química , Sesquiterpenos/química , Xantonas/química , Animales , Antimaláricos/química , Antineoplásicos/química , Estructura Molecular , Poríferos/química , Sesquiterpenos/síntesis química , Estereoisomerismo , Xantonas/síntesis químicaRESUMEN
[structure: see text]. The tetracyclic ketal 24, a suitable intermediate for the synthesis of antitumor pentacyclic quassinoids, has been efficiently prepared from communic acids (5a-c), via methyl ketone 9. The synthetic sequence from 9 to 24 consists of 15 steps in 12% overall yield.
Asunto(s)
Antineoplásicos Fitogénicos/síntesis química , Diterpenos/síntesis química , Cuassinas , Plantas Medicinales/química , TerpenosRESUMEN
The hexane extract of aerial parts of Santolina rosmarinifolia subsp. canescens afforded eight new sesquiterpenes in addition to known compounds. Their structures were determined by spectroscopic methods and chemical transformations. The conformational analysis of the germacrane constituents was carried out by spectroscopic methods, including NMR at varying temperature and by molecular mechanics calculations. The antifeedant, antibacterial and antitumoral activity of selected compounds has been tested.
Asunto(s)
Asteraceae/química , Sesquiterpenos/química , Animales , Antiinfecciosos/química , Antiinfecciosos/aislamiento & purificación , Antiinfecciosos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Ratones , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Células Tumorales CultivadasRESUMEN
A new synthetic strategy toward puupehenone-related bioactive metabolites from sclareol oxide, based on a Diels-Alder cycloaddition approach, is described. Utilizing this, marine ent-chromazonarol and the potent angiogenesis inhibitor 8-epipuupehedione have been synthesized.
Asunto(s)
Inhibidores de la Angiogénesis/síntesis química , Química Orgánica/métodos , Sesquiterpenos/metabolismo , Terpenos/síntesis química , Xantonas/metabolismo , Inhibidores de la Angiogénesis/química , Sesquiterpenos/química , Terpenos/química , Xantenos/síntesis química , Xantonas/químicaRESUMEN
The neutral fraction of the hexane extract of the aerial parts of Santolina viscosa afforded eight new longipinene derivatives (1-8), oblongifolidiol (9), and several other known compounds. The structures of 1-8 were established by spectroscopic methods and chemical transformations. The vulgarone A-type structure previously reported for oblongifolidiol has been reassigned as the longipinene derivative 9 using 2D NMR, chemical correlations, and X-ray diffraction.