Model Study toward Total Synthesis of Dimeric Pyranonaphthoquinones: Synthesis of Hemi-Actinorhodin

Abstract

Abstract In connection with our synthetic study toward the dimeric pyranonaphthoquinone antibiotics, actinorhodin (1) and β-naphthocyclinone (3), we describe herein the synthesis of a monomer, hemi-actinorhodin (6) as a model target. Several implications were gained, including (1) stereoselective synthesis of the pyranonaphthoquinone, (2) viable construction of the naphthazarin core, and (3) the final deprotection conditions.