beta-Silyl Styrene As a Dienophile in the Cycloaddition with 3,5-Dibromo-2-pyrone for the Total Synthesis of (+/-)-Pancratistatin

Abstract

A new synthetic route to (±)-pancratistatin was devised utilizing β-silyl styrene as a dienophile in the cycloaddition with 3,5-dibromo-2-pyrone. The TMS group incorporated in the cycloadduct permitted a facile elimination process for the eventual installation of the C(1)–OH function. Subsequent transformations including Curtius rearrangement and Bischler–Napieralski reactions completed the total synthesis of (±)-pancratistatin.