title: Synthesis of indole substituted twistenediones from a 2-quinonyl boronic acid.
abstract: Indole substituted twistane-like derivatives resulted in a reaction between 3,5-dimethyl-2-quinonyl boronic acid and 2-alkenyl indoles. Their MCPBA oxidation gave 6/6/9 caged systems. Boronic acid acts as a temporal promoter allowing a site-selective conjugate addition of the heteroaromatic system to the methyl substituted C-3 quinone carbon, giving an intermediate diene which is regioselectively trapped by intramolecular [4 + 2] cycloaddition.
authors.affiliation: Departamento de Química Orgánica (Módulo 01), Universidad Autónoma de Madrid , C/Francisco Tomás y Valiente 7, Cantoblanco, 28049-Madrid, Spain.
authors.forename: Jaime
authors.initials: J
authors.lastname: Rojas-Martín
authors.forename: Marcos
authors.initials: M
authors.lastname: Veguillas
authors.forename: María
authors.initials: M
authors.lastname: Ribagorda
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Carreño