The diastereospecific formation of β-N-glycoside-linked α-amino-2(5H)-furanone has been achieved with high yield via a vinylogous Mannich reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and ZnCl(2)·Et(2)O as a promoter in Et(2)O. Imines 3 of aromatic compounds and trimethylsiloxyfuran 4 were converted to N-galactosyl α-amino-2(5H)-furanone 5, ...

Three new γ-butenolide derivatives 1–3, named spiculisporic acids B–D, were isolated from the culture of Aspergillus sp. HDf2, a marine-derived fungus that resides in the sea urchin, Anthocidaris crassispina. The structures of 1–3 were elucidated on the basis of spectroscopic methods, including MS and 2D NMR techniques. Their in vitro cytotoxic activities against two cell...

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 com...

Acetogenins isolated from the Annonaceae family of tropical trees have drawn considerable attention owing to their broad spectrum of biological activities. They are structurally characterized by the presence of one to three tetrahydrofuran rings in the center of a long (partly hydroxylated) hydrocarbon chain that ends in a (functionalized) butenolide moiety. Here we describe some of our results...

A series of nine 2-arylidene-4-(4methoxy/phenoxy-phenyl)but-3-en-4-olides (I-IX) were screened against Pheretima posthuma earthworm species to assess the anthelmintic activity of the synthetic derivatives. The in vitro effects of compounds were evaluated at a concentration of 2mg/mL and time taken by the derivatives to paralyze and subsequently kill the worms was recorded. Synthetic butenolide ...

• The BC-rings of canonical SL was constructed by the acid-mediated cascade cyclization. An 18-hydroxycarlactonoate derivative successfully converted to rac -4DO/5DS. cyclization demonstrated “in flask” may be analogous that in planta . 4π-electrocyclic reaction-based mechanism is proposed. Strigolactones are a group apocarotenoids known as rhizosphere semiochemicals and phytohormones. Canonica...

Ligubenzocycloheptanone A (1), a novel tricyclic butenolide with a 6/7/5-membered ring skeleton, was isolated from the rhizome of Ligusticum chuanxiong. Its unusual structure was determined using UV, IR, HRESIMS, 1D and 2D NMR data, X-ray diffraction crystallography and by the comparison of experimental and calculated electronic circular dichroism (ECD) spectra. 1 possessed a benzocycloheptanon...