Issue 1, 2015

Synthesis of maculalactone A and derivatives for environmental fate tracking studies

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

Supplementary files

Article information

Article type
Paper
Submitted
25 Sep 2014
Accepted
20 Oct 2014
First published
20 Oct 2014
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2015,13, 199-206

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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