Improved total synthesis of (±)-Tetragocarbone A

Abstract

Stereoselective total synthesis of (±)-tetragocarbone A isolated from the propolis of an Australian stingless bee, Tetragonula carbonaria, has been developed by focusing on the latent symmetry of 1. The requisite 1R*, 3R*, 6S* stereogenic centers were selectively installed by hydroxy group directing reactions including the late stage desymmetrization of the 1,3-diketone. The target natural product was successfully prepared in 12 steps from phloroglucinol on 300 mg.