Total Synthesis of Carpacin and its Geometric Isomer as a Cancer Chemopreventer

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.