Organic & Biomolecular Chemistry
2015-03-21
One-step protecting-group-free synthesis of azepinomycin in water.
Adam J Coggins, Derek A Tocher, Matthew W Powner
Index: Org. Biomol. Chem. 13(11) , 3378-81, (2015)
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Abstract
We report an efficient, atom economical general acid-base catalyzed one-step multi-gram synthesis of azepinomycin from commercially available compounds in water. We propose that the described pH-dependent Amadori rearrangement, which couples an amino-imidazole and simple sugar, is of importance as a potential step toward predisposed purine nucleotide synthesis at the origins of life.
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