Synthesis and biological properties of new α-methylene-γ-butyrolactones and α,β-unsaturated δ-lactones

An Efficient DABCO-Catalyzed Ireland-Claisen Rearrangement of Allylic Acrylates

“…For example, they can be employed as precursors for the constructions of a-methylene-g-butyrolactones, 10,19 a family that has created considerable attention over the years since this kind of ring is a ubiquitous subunit in a wide variety of biologically active natural products. 20 Our protocol is especially attractive since the reaction conditions are mild, and all of the reagents are inexpensive and oxygeninsensitive, hence without the necessity for rigorous solvent purification and degassing associated with the use of trialkylphosphines. We are currently investigating the scope and limitations of this DABCO-catalyzed process with respect to other unsaturated allylic esters as substrates.…”

Furanose C—C‐linked γ‐lactones: a combined ESI FTICR MS and semi‐empirical calculations study

“…[3] This moiety confers a wide variety of biological properties such as cytotoxic, [4 -7] antifeeding, [8] phytotoxic and antibacterial, [9] antifungal, [10] insecticidal, [11] antiinflammatory, [12] and analgesic effects. [13] There are reports in the literature describing the potential use of compounds with this moiety as antitumor agents, [7,12] phospholipase A2 and cyclooxygenase inhibitors, [9] and antibiotics. [9] The conjugated system can act as a Michael acceptor for the addition of protein functional groups playing a fundamental role in determining bioactivity.…”

Synthesis and Biological Evaluation of Sugars Containing α,β‐Unsaturated γ‐Lactones

“…Some of these compounds were reported to be potential antitumor agents, [3] cyclooxygenase or phospholipase A2 inhibitors, [4] or antibiotics. [5] In particular sugars bearing this moiety have become important molecular targets with respect to their significant biological profile and their functionalized nature, which make them suitable intermediates of distinct synthetic versatility.…”