Total synthesis of chrysamide B

We report an efficient synthesis of the dimeric trans-epoxyamide chrysamide B, recently isolated from the deep-sea-derived fungus Penicillium chrysogenum SCSI041001. Our synthetic strategy exploits a convergent approach using solid,phase peptide synthesis for the piperazine core and a Sharpless-Katsuki epoxidation to prepare the chiral epoxyacid. The double amidation final step provides chrysamide B that was thoroughly characterized with all spectra identical to those of the natural sample. The approach was devised to facilitate the preparation of a library of analogs of chrysamide B. (C) 2017 Elsevier Ltd. All rights reserved.