Total Synthesis of (−)-Elodeoidins A and B

Abstract

Biomimicry has long been a valuable approach for designing efficient synthetic strategies in complex natural product synthesis. However, abiotic yet powerful transforms can significantly streamline the synthesis by introducing greater convergence to the synthetic route. Herein, we delineate a convergent total synthesis of elodeoidins A and B, enabled by a cross-dehydrogenative coupling (CDC) reaction between an aldehyde and an electron-deficient olefin. The CDC reaction operating under the newly discovered reaction conditions proceeds via distinct concerted deprotonation within the formal Cu(III) catalytic complex. Furthermore, the total synthesis of both structural candidates of elodeoidin B revealed that the natural product exists as a mixture of epimers at the C8 stereocenter.