57740-69-9

Upstream product

• 131146-48-0 6-benzylidene-3-methoxy-4-phenylpyran-2,5-dione 
• 6838-54-6 3-hydroxy-1,4-diphenyl-2-butanone 
• 131146-48-0 3-methoxy-4-phenyl-6-(phenylmethylene)-2H-pyran-2,5(6H)-dione 
• 57740-67-7 3,4-dehydro-3-hydroxy-5-oxo-4-phenyl-δ-valerolactone 
• 100-52-7 benzaldehyde 
• 103-80-0 phenylacetyl chloride 
• 100-44-7 benzyl chloride 
• 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 
• 131146-44-6 3-methoxy-4-phenyl-6-(phenylmethyl)-2H-pyran-2,5(6H)-dione 
• 131146-41-3 3-hydroxy-4-phenyl-6-(phenylmethyl)-2H-pyran-2,5(6H)-dione 
• 93554-96-2 α-<(trimethylsilyl)oxy>benzenepropanenitrile 
• 122-78-1 phenylacetaldehyde 
• 1589-82-8 phenylmagnesium bromide 

Downstream Products

• 548-59-4 2,5-dihydroxy-3,6-diphenyl-1,4-benzoquinone 
• 114590-95-3 5-hydroxy-3,4,7-triphenylbenzofuran-2,6-dione 
• 7611-34-9 xylerythrin 
• 26548-70-9 (E)-5-(α-carboxybenzylidene)-4-hydroxy-3-phenylfuran-2(5H)-one 
• 521-52-8 vulpic acid 
• 6273-79-6 Pulvinic acid lacton 
• 22628-22-4 (E)-4-methoxy-5-(α-methoxycarbonylbenzylidene)-3-phenylfuran-2(5H)-one 
• 137532-17-3 3-(4-aminophenyl)-5-hydroxy-4,7-diphenylbenzofuran-2,6-dione 

Relevant academic research and scientific papers

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.

SYNTHESIS OF GREVILLINS AND THEIR BIOGENETIC INTERRELATIONSHIP WITH TERPHENYLQUINONES, XYLERYTHRINS AND PULVINIC ACIDS

A synthesis of the grevillin group , of pigments present in fungi, using benzylacyloins, viz (9), as key intermediates is described, and the biogenetic interrelationships between them and the terphenylquinone, xylerythrin and pulvinic acid families of natural colouring matter, are exemplified with the in vitro conversions (16)-(17), (17)-(20) and (17)-(22).

Fungal Pigments, 49. - Synthesis of Grevillins and Related 2H-Pyran-2,5(6H)-diones

A convergent synthesis of grevillins 1 starts from diazoesters 6 which are converted into 3-aryl-2-oxopropyl ethyl oxalates 4 via bromoketones 7.Cyclization of 4 leads to pyrandiones 2 which are condensed with aromatic aldehydes to yield 4-aryl-2-benzylid