An analogue of the Streptomyces metabolite JBIR-141, featuring a delicate N-nitrosohydroxylamine, a 3-acyltetramic acid, and an oxazoline, was synthesized by a convergent strategy from L-alanine, L-threonine, and L-glutamic acid. Key steps were the cyclization of an Ala−Thr derivative to give the oxazoline, a Dieckmann condensation affording the 3-acyltetramic acid, and the N-nitrosation of a hydroxylamino derivative of glutamic acid. An adequate protecting group strategy was established for coupling the three building blocks.Letter pubs.acs.org/OrgLett
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.