Synthetic Approach to the Natural N‑Nitrosohydroxylamino Tetramic Acid JBIR-141

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 ox...

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Bibliographic Details
Published in:Organic letters 2022-07, Vol.24 (28), p.5171-5175
Main Authors: Wittmann, Lea, Wachter, Anja C., Schrey, Hedda, Schobert, Rainer
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02006