58588-90-2

Upstream product

• 109765-92-6 α-hydroxymethyl-γ-crotonolactone 
• 547-65-9 α-methylene-γ-butyrolactone 
• 917506-89-9 methyl 4-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylenebutyrate 
• 109765-91-5 4,5-dihydro-3-(1-hydroxymethyl)-3-phenylthio-3H-furan-2-one 

Downstream Products

• 1309689-82-4 C₁₂H₁₇NO₂S₂ 
• 1309689-87-9 C₁₃H₁₃NO₂S₂ 
• 1309689-88-0 C₁₂H₁₀ClNO₂S₂ 
• 1309689-78-8 C₈H₁₁NO₂S₂ 
• 1309689-86-8 C₁₂H₁₁NO₂S₂ 
• 1309689-89-1 C₁₃H₁₃NO₂S₂ 
• 1311188-75-6 4-hydroxymethyl-5-(5-isopropenyl-2-methyl-3-oxo-cyclopentyl)-3-phenoxymethyl-dihydro-furan-2-one 
• 1311188-77-8 4-hydroxy-9-methyl-6-methylene-3-phenylsulfanyl-methyl-octahydro-azuleno[4,5-b]furan-2,8-dione 

Relevant academic research and scientific papers

Total syntheses of paraconic acids and 1,10-seco-guaianolides via a barbier allylation/translactonization cascade of 3-(Bromomethyl)-2(5H)-furanone

A palladium-catalyzed Barbier allylation/translactonization cascade reaction was established for the rapid construction of β,γdisubstituted α-exo-methylene-γ-butyrolactone, an important motif in sesquiterpenes. Dimethyl zinc played significant roles in bo

Discovery and synthesis of novel indole derivatives-containing 3-methylenedihydrofuran-2(3H)-one as irreversible LSD1 inhibitors

Lysine-specific demethylase 1 (LSD1), demethylase against mono- and di - methylated histone3 lysine 4, has emerged as a promising target in oncology. More specifically, it has been demonstrated as a key promoter in acute myeloid leukemia (AML), and several LSD1 inhibitors have already entered into clinical trials for the treatment of AML. In this paper, a series of new indole derivatives were designed and synthesized based on a lead compound obtained by a high-throughput screening with our in-house compound library. Among the synthetic compounds, 9e was characterized as a potent LSD1 inhibitor with an IC50 of 1.230 μM and can inhibit the proliferation of THP-1 cells effectively. And most importantly, this is the first irreversible LSD1 inhibitor that is not derived from monoamine oxidase inhibitors. Hence, the discovery of 9e may serve as a proof of concept work for AML treatment.

Rapid and scalable synthesis of chiral bromolactones as precursors to α-exo-methylene-γ-butyrolactone-containing sesquiterpene lactones

The sesquiterpene lactones cover a diverse and pharmacologically important diversity space. In particular, the electrophilic α-exo-methylene-γ-butyrolactone moiety that is preponderant in this natural product family has been shown to readily engage in cov

Application of the palladium-catalysed norbornene-assisted catellani reaction towards the total synthesis of (+)-linoxepin and isolinoxepin

Our ongoing effort towards the development of highly selective transition-metal-catalysed C-H activation processes has led to the expansion of the Catellani reaction. In a Pd0/PdII/Pd IV-catalysed domino reaction, an aryl iodide, alkyl iodide and tert-butyl acrylate were combined to synthesize the carbon framework of the novel lignan (+)-linoxepin. The enantioselective synthesis highlights the work accomplished in our group and provides an excellent procedure for the reliable and scalable synthesis of architecturally complex scaffolds. This report outlines the synthetic approaches towards this interesting class of biologically active molecules. After the key Catellani/Heck reaction, our synthesis features a Leimeux-Johnson oxidation and a titanium tetrachloride mediated aldol condensation. Finally, a tuneable Mizoroki-Heck reaction was performed to furnish not only the natural product (+)-linoxepin but also its isoform, which we have named isolinoxepin. The enantioselective total synthesis of the natural product (+)-linoxepin has been accomplished in eight steps starting from commercial materials. The key Pd-catalysed Catellani step served to combine aryl iodide, alkyl iodide and tert-butyl acrylate in a domino sequence. By tuning the final Heck reaction, both the natural product and its structural isomer were synthesized. Copyright

Asymmetric synthesis of β-substituted α-methylenebutyro-lactones via trip-catalyzed allylation: Mechanistic studies and application to the synthesis of (S)-(-)-hydroxymatairesinol

Asymmetric allylation of (hetero)aromatic aldehydes by a zinc(II)-allylbutyrolactone species catalyzed by a chiral BINOL-type phosphoric acid gave β-substituted α-methylenebutyrolactones in 68 to >99% ee and 52-91% isolated yield. DFT studies on the intermediate Zn 2+-complex - crucial for chiral induction - suggest a six-membered ring intermediate, which allows the phosphoric acid moiety to activate the aldehyde. The methodology was applied to the synthesis of the antitumour natural product (S)-(-)-hydroxymatairesinol.

Stereoselective synthesis of β-(hydroxymethylaryl/alkyl)-α- methylene-γ-butyrolactones

Zinc or a chromium(II) source with 3-(bromomethyl)furan-2(5H)-one (3) and an aldehyde gives β-(hydroxymethylaryl/alkyl)-α-methylene-γ- butyrolactones 5 in good yields and high diastereoselectivities. The methodology is demonstrated in concise syntheses of (±)-hydroxymatairesinol (8) and (±)-methylenolactocin (10) by subsequent arylboronate conjugate addition and translactonization, respectively.

Synthesis and in vitro antitumor activity of new butenolide-containing dithiocarbamates

Three series of butenolide-containing dithiocarbamates were designed and synthesized. Their anti-tumor activity in vitro was evaluated. Among them compound I-14 exhibited broad spectrum anti-cancer activity against five human cancer cell lines with IC50 30 μM. Structure-activity relationship analysis showed that the introduction of dithiocarbamate side chains on the C-3 position of butenolide was crucial for anti-tumor activity.

Concise total synthesis of (-)-8-epigrosheimin

A highly efficient route was developed to synthesize (-)-8-epigrosheimin in four steps from aldehyde 2 based on a substrate-controlled method. The key steps of the synthesis included (1) a stereo- and regioselective allylation addition, (2) an intramolecular translactonization, and (3) an aldehyde-ene cyclization.

Syntheis of 3-(1-Hydroxyalkyl)-5H-furan-2-ones: Study of their Reaction with Halogens

The syntheis of 3-(1-hydroxyalkyl)-5H-furan-2-ones, 4a-c, is reported.The reaction of lactones 4a and 4b with bromine under typical ionic bromination conditions gives as major product the unexpected substitution of the allylic hydroxyl group.Only the less hindered double bond in 4c gives some proportion of the normal addition product.The bromine chloride addition to 4c proceeds with 55 percent yield, while lactone 4a does not add BrCl.All these results point to the fact that halogen addition to the double bond of 4 suffers at least from steric hindrance.Key words: 3-(1-hydroxyalkyl)-5H-furna-2-ones; bromination; bromine chlorination

Synthesis of 3-(1-Hydroxyalkyl)furan-2-(5H)-ones: Unexpected Substitution Reaction in Allylic Alcohols by Bromine

Substitution of an allylic hydroxyl group on α,β-butenolide derivatives by bromine under typical ionic bromination conditions is reported.