α-Methylene-γ-butyrolactones [dihydro-3-methylene-2(3H)furanones] constitute an important group of natural products and possess wide-ranging biological activities. Progress in the synthesis of the heterocycle and the classification of the synthetic methods are not only of practical interest, but also fundamentally important as a current example for the construction of an unusual 1,4-functionality distance and an α-substituted acrylic ester moiety which is susceptible to nucleophilic attack.

Synthesis and Biological Activity of α‐Methylene‐γ‐butyrolactones

Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions.

A review of natural products and plants as potential antidiabetic drugs.

https://www.repositorio.ufop.br/bitstream/123456789/805/6/ARTIGO_TrioxygenatedNaturallyOccurring.pdf

Tetraoxygenated naturally occurring xanthones

Copper radionuclides and radiopharmaceuticals in nuclear medicine

Goniothalenol: a novel, bioactive, tetrahydrofurano-2-pyrone from (annonaceae)

Syntheses via vinyl sulfones. 11. A triply convergent total synthesis of L-(-)-prostaglandin E2

Structure and stereochemistry of psorospermin and related cytotoxic dihydrofuranoxanthones from Psorospermum febrifugum

Saudin, a hypoglycemic diterpenoid, with a novel 6,7-seco-labdane carbon skeleton, from Cluytia richardiana

The alpha-methylene lactones 9, 12, 21, and 24 were prepared by a mild, convenient alpha-methylenation process using the alpha-ethyloxalyl derivatives in nonoptimized yields ranging from 23 to 90%. The rates of reaction of these and several other lactones with cysteine at pH 7.4 and their KB toxicities were measured. These studies showed that neither the strained trans-fused alpha-methylene lactone 12 nor the hydroxy-alpha-methylene lactones 5 and 6 reacted with cysteine with rates comparable to elephantopin. Based on these limited studies, the rate of cysteine addition appears to be relatively insensitive to changes in strain energy and neighboring groups. In addition, the rate constant for reaction with cysteine did not correlate with cytotoxicity.

Ann T. McKenzie

Papers

Goniothalenol: a novel, bioactive, tetrahydrofurano-2-pyrone from (annonaceae)

Syntheses via vinyl sulfones. 11. A triply convergent total synthesis of L-(-)-prostaglandin E2

Structure and stereochemistry of psorospermin and related cytotoxic dihydrofuranoxanthones from Psorospermum febrifugum

Saudin, a hypoglycemic diterpenoid, with a novel 6,7-seco-labdane carbon skeleton, from Cluytia richardiana

Potential antitumor agents. Synthesis, reactivity, and cytotoxicity of .alpha.-methylene carbonyl compounds