From aerial parts of Austroeupatorium inulifolium was isolated the ent-nor-furano triol labdane austroeupatol 1.The compound 1 was treated with IBX showing an unexpected selectivity at the potentially oxidizable sites...From aerial parts of Austroeupatorium inulifolium was isolated the ent-nor-furano triol labdane austroeupatol 1.The compound 1 was treated with IBX showing an unexpected selectivity at the potentially oxidizable sites of the sub-strate yielding the 2-oxoaustroeupatol(2)and 2,19-dioxoaustroeupatol(3).The treatment of 2 with sodium periodate yields a heterocyclic derivative(ε-caprolactone derivate 4)formed by oxidative cleavage and unexpected intramo-lecular attack of the hydroxymethylene(C-19)oxygen to the ketonic carbon(C-2).A plausible mechanistic pathway for the obtention of compound 4 is proposed.展开更多
基金supported by the National Fund of Science,Technology and Innovation (FONACIT) (Grant N°201300288)within the framework of the project PCP France-Venezuelaby the CDCHTA-ULA (Grant N°C-1935-15-08-ED).
文摘From aerial parts of Austroeupatorium inulifolium was isolated the ent-nor-furano triol labdane austroeupatol 1.The compound 1 was treated with IBX showing an unexpected selectivity at the potentially oxidizable sites of the sub-strate yielding the 2-oxoaustroeupatol(2)and 2,19-dioxoaustroeupatol(3).The treatment of 2 with sodium periodate yields a heterocyclic derivative(ε-caprolactone derivate 4)formed by oxidative cleavage and unexpected intramo-lecular attack of the hydroxymethylene(C-19)oxygen to the ketonic carbon(C-2).A plausible mechanistic pathway for the obtention of compound 4 is proposed.
