RESUMEN
We report a full account of our work towards the development of Mo-catalyzed asymmetric allylic alkylation reactions with 3-alkyloxindoles as nucleophiles. The reaction is complementary to the Pd-catalyzed reaction with regard to the scope of oxindole nucleophiles. A number of 3-alkyloxindoles were alkylated successfully under mild conditions to give products with excellent yields and good-to-excellent enantioselectivities. Applications of this method to the preparation of indoline alkaloids such as (-)-physostigmine, ent-(-)-debromoflustramineâ B, and the indolinoquinoline rings of communesinâ B are reported.
Asunto(s)
Alcaloides/síntesis química , Compuestos Heterocíclicos de 4 o más Anillos/síntesis química , Hidrocarburos Halogenados/síntesis química , Indoles/síntesis química , Molibdeno/química , Fisostigmina/síntesis química , Alcaloides/química , Alquilación , Catálisis , Compuestos Heterocíclicos de 4 o más Anillos/química , Hidrocarburos Halogenados/química , Indoles/química , Estructura Molecular , Molibdeno/metabolismo , Oxindoles , Fisostigmina/análogos & derivados , Fisostigmina/química , EstereoisomerismoRESUMEN
An expedient route to the Calabar bean alkaloids (-)-physovenine and (-)-physostigmine has been devised using a chiral building block which was originally designed for diastereocontrolled construction of aldohexoses.