First total synthesis of aerucyclamide B

The first total synthesis of the antimalarial aerucyclamide B has been achieved in 9% overall yield. Two thiazoles and a dipeptide were used to prepare two open precursors of cyclo-Gly-L-allo-Thr-L-Ile-Thz-D-allo-Ile-Thz. Cyclodehydration with Deoxo-Fluor of the beta-hydroxyamide present in the macrocycle, rendered aerucyclamide B (67%) and an unexpected fluorous derivative (28%). (C)13 Elsevier Ltd. All rights reserved.