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Issue 1, 2015
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Synthesis of maculalactone A and derivatives for environmental fate tracking studies

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Abstract

Maculalactone A (1) constitutes a promising antifouling agent, inhibiting the formation of biofilms in marine and freshwater systems. In this study, we developed a new route, based on a late-stage formation of the butenolide core, leading to the total synthesis of maculalactone A (three steps, overall yield of 45%) and delivering material on a gram scale. In addition, analogues of the title compound were assayed concerning their biological activity, utilizing Artemia franciscana and Thamnocephalus platyurus. The most active analogue was functionalized with a rhodamine B fluorophore and was utilized in an in vivo staining experiment in Artemia salina. Two different tissues were found to accumulate this maculalactone A derivative.

Graphical abstract: Synthesis of maculalactone A and derivatives for environmental fate tracking studies

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Supplementary files

Article information


Submitted
25 Sep 2014
Accepted
20 Oct 2014
First published
20 Oct 2014

This article is Open Access

Org. Biomol. Chem., 2015,13, 199-206
Article type
Paper
Author version available

Synthesis of maculalactone A and derivatives for environmental fate tracking studies

S. L. Bader, M. U. Luescher and K. Gademann, Org. Biomol. Chem., 2015, 13, 199
DOI: 10.1039/C4OB02042A

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