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Org Biomol Chem. 2010 Oct 7;8(19):4243-5. doi: 10.1039/c0ob00037j. Epub 2010 Aug 6.

First synthetic entry to the trimer stage of 5,6-dihydroxyindole polymerization: ortho-alkynylaniline-based access to the missing 2,7':2',7''-triindole.

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1
Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Complesso Universitario Monte S. Angelo, via Cintia 4, I-80126, Naples, Italy.

Abstract

5,6-Dihydroxyindole oligomers are valuable synthetic targets for the structural characterization of eumelanin biopolymers as well as for the realization of bioinspired functional materials. An ortho-alkynylaniline-based strategy allowed the first access to a trimer, the missing 5,5',5'',6,6',6''-hexaacetoxy-2,7':2',7''-triindole, and its detection as a minor intermediate en route from 5,6-dihydroxyindole to eumelanin-like polymers.

PMID:
20689895
DOI:
10.1039/c0ob00037j
[Indexed for MEDLINE]
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