Synthesis of the C1–C18 Fragment of Rhizopodin: Late-State Introduction of the Oxazole

Abstract

The synthesis of the C1-C18 fragment of the myxobacteria metabolite rhizopodin is described. Initial attempts at installing the E,E-diene via cross coupling with an oxazole fragment gave poor results. An alternative approach, in which the diene was formed prior and the oxazole introduced by an acylation/O,N-shift protocol, gave the C1-C18 fragment 2 of rhizopodin (1).