22628-22-4

Upstream product

• 186581-53-3 diazomethane 
• 521-52-8 vulpic acid 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 137531-74-9 5-dimethoxyphosphoryl-4-methoxy-3-phenylfuran-2(5H)-one 
• 98-80-6 phenylboronic acid 
• 704890-29-9 (3-methoxy-5-oxo-4-trifluoromethanesulfonyloxy-5H-furan-2-ylidene)-phenyl-acetic acid methyl ester 
• 704890-25-5 4-methoxy-3-oxo-2-phenyl-butyric acid methyl ester 
• 704890-26-6 (Z)-4-Methoxy-2-phenyl-3-trimethylsilanyloxy-but-2-enoic acid methyl ester 
• 704890-28-8 (4-hydroxy-3-methoxy-5-oxo-5H-furan-2-ylidene)-phenyl-acetic acid methyl ester 
• 704890-27-7 {(E)-3-Methoxy-1-[1-methoxy-1-trimethylsilanyloxy-meth-(Z)-ylidene]-2-trimethylsilanyloxy-allyl}-benzene 
• 35369-28-9 2-methoxy-3-phenylmaleic anhydride 
• 131146-48-0 6-benzylidene-3-methoxy-4-phenylpyran-2,5-dione 
• 137532-11-7 3-oxo-1,4-diphenylbutan-2-yl ethyl oxalate 
• 131146-47-9 6-bromo-3-methoxy-4-phenyl-6-(phenylmethyl)-2H-pyran-2,5(6H)-dione 

Downstream Products

• 521-52-8 vulpic acid 
• 26548-70-9 (E)-5-(α-carboxybenzylidene)-4-hydroxy-3-phenylfuran-2(5H)-one 

Relevant academic research and scientific papers

Suzuki cross-coupling reactions of γ-alkylidenebutenolides: Application to the synthesis of vulpinic acid

α-Hydroxy-γ-alkylidenebutenolides were efficiently functionalized by Suzuki cross-coupling reactions via the corresponding enol triflates. The natural product vulpinic acid was prepared by this methodology.

Synthesis of Grevillins, Novel Pyrandione Pigments of Fungi. Biogenetic Interrelationships between Grevillins, Pulvinic Acids, Terphenylquinones and Xylerythrins

A synthesis of the grevillin group of pyrandione pigments, e.g. 3, 23 and 24 present in fungi is described.The synthesis, which is based on a biogenetic model, uses bis-benzylacyloins 9 and their corresponding oxalate derivatives as key intermediates (Scheme 3).Treatment of the grevillins 25a-c with sodium ethoxide in ethanol effects their quantitative isomerisation into the corresponding terphenylquinone pigments 4a-c.Perkin-type condensations between the terphenylquinones 4 and arylacetic acids in the presence of sodium acetate-acetic anhydride then produces the xylerythrin pigments 29a-e, whereas rearrangements of 4 in the presence of dimethyl sulphoxide leads to pulvinic acid derivative, e.g. 31, 32 and 5.These synthetic studies interrelate the biosynthetic origins of the pigment types 3, 4, 5 and 8 together with the related pulvinones 6 and furanone 7 fungal pigments.

Maleic Anhydrides in Synthesis. Preparation of Furan-2(5H)-one Phosphonate Derivatives and a New Synthesis of Pulvinic Acids and Pulvinone Analogues

Reactions between substituted maleic anhydrides, viz. 1, and sodium dimethyl phosphite in refluxing benzene are shown to lead to the corresponding furan-2(5H)-one phosphonates 2 and 8.Wadsworth-Emmons olefination reactions involving 2 and heteroarylaldehy