title: 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.
authors.affiliation: Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland. karl.gademann@unibas.ch.
authors.forename: Samuel L
authors.initials: SL
authors.lastname: Bader
authors.forename: Michael U
authors.initials: MU
authors.lastname: Luescher
authors.forename: Karl
authors.initials: K
authors.lastname: Gademann
mesh_terms: D000818:Animals; D001156:Artemia / Q000378:metabolism; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D060326:Chemistry Techniques, Synthetic; D004777:Environment; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D008853:Microscopy; D013329:Structure-Activity Relationship
chemical_list: D001572:Benzofurans; D007783:Lactones; C544633:maculalactone A