RESUMO
A sequential CH functionalization strategy for the synthesis of the marine alkaloid dictyodendrinâ B is reported. Our synthesis begins from commercially available 4-bromoindole and involves six direct functionalizations around the heteroarene core as part of a gram-scale strategy towards the natural product.
Assuntos
Carbazóis/química , Carbazóis/síntese química , Pirróis/química , Pirróis/síntese química , Técnicas de Química Sintética , Ligação de Hidrogênio , Indóis/química , Estrutura MolecularRESUMO
In this paper, a novel synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups is presented. Anionically activated trifluoromethyl groups react with secondary amines under aqueous conditions to afford tertiary amides. The mechanism involves initial elimination of hydrogen fluoride by an E1cB mechanism to afford an electrophilic quinone methide- or azafulvene-type intermediate that reacts with secondary amines under aqueous conditions to afford the tertiary amide in good yield (up to 99%).