Synthesis and studies on the antiviral activities of substituted γ-butyrolactones and butenolides

Avetisyan, A. A.; Nazaryan, R. G.; Dzhandzhapanyan, A. N.; Votyakov, V. I.; Khlyustov, S. V.; Vladyko, G. V.; Klimovich, V. Ya.; Korobchenko, L. V.; Shashikhina, M. N.; Zhavrid, S. V.

doi:10.1007/bf00761539

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“…Among the various known methods to synthesise butenolides, only few approaches allow substituents in all three positions. For this goal, we investigated a procedure originally reported by Avetisyan et al 39 in 1981 and later utilized in an industrial setting. [35][36][37] Diene 13 was therefore synthesised in a convergent fashion from the starting material 10, which was accessed as described by Pihko et al 38 (Scheme 2).…”

Section: Improved Total Synthesis Of Maculalactone Amentioning

confidence: 99%

“…Another potentially rewarding strategy constitutes the late stage preparation of the olefinic bond through an elimination approach. For this goal, we investigated a procedure originally reported by Avetisyan et al 39 in 1981 and later utilized in an industrial setting. 40 Key to this strategy is the intramolecular cyclization of 3,6-dioxo-4-oxa-1-hexanoate derivative, 17, with a subsequent loss of ethanol and CO 2 , furnishing the desired butenolide (Scheme 3).…”

Section: Improved Total Synthesis Of Maculalactone Amentioning

confidence: 99%

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Synthesis of maculalactone A and derivatives for environmental fate tracking studies

2015

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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.

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