title: A Synthesis of the Tricyclic Core Structure of FR901483 Featuring an Ugi Four-Component Coupling and a Remarkably Selective Elimination Reaction.
abstract: Three key reactions, an efficient Ugi four-component coupling, a regiospecific, base-mediated elimination reaction, and an intramolecular nitrone/alkene [3+2] cycloaddition, were used to achieve an effective synthesis of the tricyclic molecular framework of the immunosuppressant FR901483. The outcome of a control experiment supports the idea that an internal deprotonation by an alkoxide ion is the origin of the site selectivity observed in the base-induced elimination of hydroxy mesylate 17.
authors: Frick Chemical Laboratory, Princeton University, Princeton, NJ 08544-1009, USA, Fax +1(609)2581980.
authors: Hirofumi
authors: H
authors: Seike
authors: Erik J
authors: EJ
authors: Sorensen