Concise, aromatization-based approach to an elaborate C2-symmetric pyrenophane

Chem Commun (Camb). 2012 Aug 11;48(62):7747-9. doi: 10.1039/c2cc33611a. Epub 2012 Jul 3.

Abstract

A very short synthesis (5 steps), the crystal structure and resolution of an elaborate, inherently chiral [n](1,6)pyrenophane is reported. The synthesis hinges upon two very productive events: a multicomponent reaction and an unprecedented double-McMurry/valence isomerization/dehydrogenation step. Aromatization reactions are involved in the formation of all four of the rings of the pyrene system.