78376-11-1

Upstream product

• 69556-70-3 4-methoxy-5H-furan-2-one 
• 100-52-7 benzaldehyde 
• 82204-15-7 4-methoxy-2-(trimethylsilyloxy)furan 
• 86268-15-7 methyl 5-lithiotetronate 
• 1116-51-4 ethyl χ-bromo-β-methoxycrotonate 
• 3510-99-4 3-methoxy-but-2-enoic acid ethyl ester 

Downstream Products

• 82204-21-5 methyl 5-(1-methoxybenzyl)tetronate 
• 1448595-30-9 (Z)-5-benzylidene-3-bromo-4-methoxyfuran-2(5H)-one 
• 1448595-39-8 3,5-dibromo-5-(bromo(phenyl)methyl)-4-methoxyfuran-2(5H)-one 
• 1448595-40-1 (Z)-3-bromo-5-(bromo(phenyl)methylene)-4-methoxyfuran-2(5H)-one 
• 1448595-41-2 (E)-3-bromo-5-(bromo(phenyl)methylene)-4-methoxyfuran-2(5H)-one 
• 72031-58-4 (Z)-4-methoxy-5-benzylidenefuran-2(5H)-one 
• 100074-92-8 4-methoxy-3-phenyl-5-(phenylmethylene)furan-2(5H)-one 
• 78819-24-6 5,5-E-fadyenolide 
• 78819-23-5 5,6-Z-fadyenolide 

Relevant academic research and scientific papers

A Rapid Entry to Diverse γ-Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived γ-Lactones and Metal-Catalyzed Postfunctionalization

The synthesis of a series of diverse methyl and benzyl γ-ylidenetetronate derivatives was accomplished through the condensation of methyl and benzyl tetronates with (hetero)aryl aldehydes in a new two- or three-step aldolisation/dehydration sequence. The bromination of methyl and benzyl γ-ylidenetetronates occurred under mild conditions to provide the corresponding C-3-brominated γ-unsaturated lactones. Di- and tribrominated γ-lactones were prepared under slightly different conditions. Some brominated materials were employed in representative Stille, Suzuki-Miyaura, and Sonogashira cross-coupling reactions to yield functionalized methyl and benzyl γ-ylidenetetronate derivatives. Compounds that resulted from the Sonogashira cross-coupling reactions were desilylated and converted into 1,2,3-triazole derivatives through a copper(I)-catalyzed 1,3-dipolar cycloaddition reaction with benzyl azide.

Regioselective bromination of tetronic acid-derived γ-lactones and metal-catalyzed post-functionalization: An efficient access to new γ-ylidenetetronate derivatives

The synthesis of several methyl and benzyl γ-ylidenetetronates was accomplished and the bromination reactions of these derivatives, using bromine or N-bromosuccinimide (NBS), were found to occur under mild conditions. Several new brominated γ-unsaturated

Highly regioselective 3-hydroxyalkylations of boron 4-methoxy-2-furanolates: A new entry to 5-unsubstituted and 5-monosubstituted 3-acyl-4-o-methyl tetronates

Boron 4-methoxy-2-furanolates generated in situ from 5-unsubstituted and 5-monosubstituted 4-O-methyl tetronates undergo highly regioselective 3-hydroxyalkylations with aldehydes to give 5-unsubstituted and 5-monosubstituted 3-acyl-4-O-methyl tetronates, respectively, in good overall yields after oxidation of the intermediate alcohols with 2-iodoxybenzoic acid.

Process for the production of threo-4-alkoxy-5- (arylhydroxymethyl)-2(5H)-furanones

Threo-4-alkoxy-5-(arylhydroxymethyl)-2(5H)-furanones are obtained by condensation of 4-alkoxy-2(5H)-furanones with benzaldehydes in the presence of lithium hydroxide without contamination by the corresponding erythro stereoisomers. The condensation is pre

Synthetic Routs to the Piperolides, Faydenolides, Epoxypiperolides, and Related Compounds

Syntheses of the piperolides, the faydenolides, epoxypiperolide, and related compounds are described. (+/-)-Narthogenin is also efficiently produced.

2-TRIMETHYLSILYLOXY-4-METHOXYFURAN: AN EXCELLENT SYNTHON FOR THE PRODUCTION OF 5-SUBSTITUTED TETRONATES (4-METHOXYBUTENOLIDES).

The preparation of 2-trimethylsilyloxy-4-methoxyfuran (6) is described.Under the influence of Lewis acids, this compound is substituted by a wide variety of reagents in a regiospecific fashion at C-5 to give substituted methyl tetronates.Its utility is ex