perophoramidine and phenserine

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-(-)-debromoflustramine B, and the indolinoquinoline rings of communesin B are reported.

Topics: Alkaloids; Alkylation; Catalysis; Heterocyclic Compounds, 4 or More Rings; Hydrocarbons, Halogenated; Indoles; Molecular Structure; Molybdenum; Oxindoles; Physostigmine; Stereoisomerism