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

Coggins, AJ; Tocher, DA; Powner, MW; (2015) One-step protecting-group-free synthesis of azepinomycin in water. Organic & Biomolecular Chemistry , 13 (11) 3378 - 3381. 10.1039/c5ob00210a. Green open access

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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.

Type: Article
Title: One-step protecting-group-free synthesis of azepinomycin in water
Location: England
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/c5ob00210a
Publisher version: http://dx.doi.org/10.1039/c5ob00210a
Language: English
Additional information: Copyright © Royal Society of Chemistry 2015
UCL classification: UCL
UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/1461252
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