Issue 11, 2015

One-step protecting-group-free synthesis of azepinomycin in water

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.

Graphical abstract: One-step protecting-group-free synthesis of azepinomycin in water

Supplementary files

Article information

Article type
Paper
Submitted
02 Jan 2015
Accepted
03 Feb 2015
First published
03 Feb 2015

Org. Biomol. Chem., 2015,13, 3378-3381

One-step protecting-group-free synthesis of azepinomycin in water

A. J. Coggins, D. A. Tocher and M. W. Powner, Org. Biomol. Chem., 2015, 13, 3378 DOI: 10.1039/C5OB00210A

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