An elegant approach to a variety of Aristolactams was reported in Org Lett 2008, taking advantage of alpha-formylaromatic boronic acids and an appropriately substituted lactam. As illustrated below, initial coupling with the bromide on the advanced lactam with a variety of aryl and heteroaryl boronic acids provides a the bis-aryl coupled product which undergoes a simple aldol condensation to close the ring in a one-pot format under microwave heating at 150C in 10 minutes…..providing a route to natural aristolactams as well as an opportunity to study substitution patterns around the phenanthrene or heteraromatic fused rings.

Screen Shot 2014-11-06 at 12.18.39 PM

Advertisements