TL;DR: Carpacin (1a) as discussed by the authors is an antidepressant in Asiatic folk medicine from the Carpano tree, achieved in which the longest linear sequence is only four steps in over all yield 67% from commercially available Sesamol.
Abstract: Carpacin (1a), an antidepressant in Asiatic folk medicine from the Carpano tree, is achieved in which the longest linear sequence is only four steps in over all yield 67% from commercially available Sesamol. The key transformations in the synthesis are the selective palladium-catalyzed coupling reactions of aryl bromide with Grignard reagents. The first preparation of its geometric isomer (1b) is described. Highlights of the synthesis include Pd-catalyzed coupling, selective hydrogenation, and Wittig reactions. Carpacin was examined as a potential inhibitor of carcinogenesis.