Issue 50, 2018
From the journal:

RSC Advances

Expedient synthesis of eumelanin-inspired 5,6-dihydroxyindole-2-carboxylate ethyl ester derivatives†

Andrew H. Aebly,a   Jeffrey N. Levy,a   Benjamin J. Steger,a   Jonathan C. Quirkea  and  Jason M. Belitsky ORCID logo *a  

* Corresponding authors

a Department of Chemistry and Biochemistry, Oberlin College, 119 Woodland St., Oberlin, OH 44074, USA
E-mail: Jason.Belitsky@Oberlin.edu

Abstract

Dihydroxyindoles such as 5,6-dihydroxyindole-2-carboxylic acid (DHICA) are the main monomer units of eumelanin, the black to brown pigment in humans, and have emerging biological roles beyond melanin. Elaboration of commercially available 5,6-dimethoxy-2-carboxylate ethyl ester provides ready access to DHICA-inspired small molecules, including 3-(hetero)aryl-indoles and 4,7-di-(hetero)aryl-indoles.

Graphical abstract: Expedient synthesis of eumelanin-inspired 5,6-dihydroxyindole-2-carboxylate ethyl ester derivatives

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DOI
https://doi.org/10.1039/C8RA06148C
Article type
Paper
Submitted
20 Jul 2018
Accepted
28 Jul 2018
First published
07 Aug 2018
This article is Open Access
Creative Commons BY license

RSC Adv., 2018,8, 28323-28328

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Expedient synthesis of eumelanin-inspired 5,6-dihydroxyindole-2-carboxylate ethyl ester derivatives

A. H. Aebly, Jeffrey N. Levy, B. J. Steger, J. C. Quirke and J. M. Belitsky, RSC Adv., 2018, 8, 28323 DOI: 10.1039/C8RA06148C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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