title: One-pot synthesis of pentacyclic diamines from quinolines by a new Zn/AcOH-promoted cascade reaction.
abstract: A simple and efficient method for the one-pot synthesis of pentacyclic diamines from quinolines is described. It involves a new Zn/AcOH-promoted cascade reaction, in which two C[bond]C bonds and four to five stereogenic centers are established under mild conditions. The regiochemistry of the dimerization and cyclization step is governed by substituent effects, allowing access to a head-to-head (2, 3) or head-to-tail skeleton (4, 5).
authors.affiliation: Laboratoire de Chimie des Substances Végétales, LCSV - Institut du Pin, Université Bordeaux I, 351, Cours de la Libération, 33405 Talence-Cedex, France.
authors.forename: Jean-Christophe
authors.initials: JC
authors.lastname: Gauffre
authors.forename: Micheline
authors.initials: M
authors.lastname: Grignon-Dubois
authors.forename: Bernadette
authors.initials: B
authors.lastname: Rezzonico
authors.forename: Jean-Michel
authors.initials: JM
authors.lastname: Léger