A study in indol-2-yl carbinol chemistry and the application for the total synthesis of mersicarpine

We present an efficient protocol for the Lewis acid-catalyzed reaction of indol-2-yl carbinols with various pi-nucleophiles including the heteroarenes such as indole, pyrrole, furan, as well as the silyl vinyl ethers. Most importantly, the precise use of this protocol enabled us to establish a very concise and practical route for the total synthesis of (+/-)-mersicarpine in eight linear steps with ca. 14% overall yield from commercially available indole and succinic anhydride. Moreover, the method developed herein would be broadly applicable for the diverse synthesis of a number of structurally intriguing indole alkaloids as well as biologically interesting hetero-triarylmethanes. (C) 2014 Elsevier Ltd. All rights reserved.