22609-88-7

Upstream product

• 165337-03-1 4-(benzyloxy)-5-phenylfuran-2(5H)-one 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 105-36-2 ethyl bromoacetate 
• 33553-90-1 4-hydroxy-4-phenyl-but-2-ynoic acid methyl ester 

Downstream Products

• 69556-74-7 (+/-)-4-Ethoxy-5-phenyl-2,5-dihydrofuran-2-one 
• 80936-01-2 3-[1-(4-Chlorphenyl)-butyl]-4-hydroxy-5-phenyl-2,5-dihydrofuran-2-on 
• 22609-96-7 4-methoxy-5-phenylfuran-2(5H)-one 

Relevant academic research and scientific papers

A convenient entry to 5-(sp2)-substituted and 5,5-disubstituted tetronic acids

A one-pot, convenient and general access to 5-sp2-substituted and 5,5-disubstituted tetronic acids is described. The protocol embodies two consecutive chemical events: a Michael addition of pyrrolidine on a secondary or tertiary γ-hydroxy-α,β-a

Tipranavir analogous 3-sulfonylanilidotetronic acids: new synthesis and structure-dependent anti-HIV activity

Sulfonamide-containing tetronic acids 1, structural analogues of the HIV-1 protease inhibitor tipranavir, were synthesised in five steps including a microwave-assisted Claisen rearrangement of cinnamyl tetronates and a modified Charette cyclopropanation of the so-formed 3-allyltetronic acids. Compounds 1 with two non-H residues (R1, R2) at C-5 of the tetronate core exhibited structure-dependent antiviral activity in two HIV strains. Derivatives 1c (R1=R2=Me, R3=Cl) and 1d (R1,2=(CH2)5, R3=Me) were most active (IC50NL4-3.

REACTION OF O-TRIMETHYLSILYLATED CYANOHYDRINS WITH α-BROMOESTERS: A NEW SYNTHESIS OF TETRONIC ACIDS

Tetronic acids and β-keto-γ-butyrolactones are easily prepared by the zinc induced reaction of O-trimethylsilylated cyanohydrins and α-bromoesters.