A Revised Protecting Group Strategy Enables a Divergent Synthesis of Prenylated Isoflavones from Psoralea corylifolia

Abstract

Three bioactive prenylated isoflavone natural products were synthesized for the first time, using a combination of Pd-catalyzed Suzuki–Miyaura coupling for installing the B-ring, microwave-promoted Claisen rearrangement of allyl ethers, and Ru-catalyzed olefin cross me tathesis for obtaining the prenyl substituents. Careful consideration of the protecting group strategy turned out to be vital for the success of these total syntheses.

Description

Keywords

isoflavones, Suzuki coupling, Claisen rearrangement, ole fin metathesis, protecting groups

Citation

von Chamier Gliszczinski, S., Sperlich, E., Kelling, A., Kwesiga, G., & Schmidt, B. (2025). A Revised Protecting Group Strategy Enables a Divergent Synthesis of Prenylated Isoflavones from Psoralea corylifolia. Synthesis, 57(11), 1833-1847.