A Concise Synthetic Approach to the Sorbicillactones: Total Synthesis of Sorbicillactone A and 9-<i>epi</i>-Sorbicillactone A

Abstract

A concise (12 step) total synthesis of sorbicillactone A and 9-epi-sorbicillactone A is reported. Unlike typical routes to the sorbicillinoids, this strategy does not start from sorbicillin and allows for the production of the bicyclic core on a multigram scale. The intramolecular conjugate addition of a tethered malonate serves as an effective means of introducing the lactone ring and provides a synthetic handle for installing the amide nitrogen.