114590-91-9Relevant academic research and scientific papers
Synthesis of Grevillins, Novel Pyrandione Pigments of Fungi. Biogenetic Interrelationships between Grevillins, Pulvinic Acids, Terphenylquinones and Xylerythrins
Pattenden, Gerald,Pegg, Neil A.,Kenyon, Ronald W.
, p. 2363 - 2372 (2007/10/02)
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.
Pigments of Fungi. XV An Efficient, Unambiguous Route to Unsymmetrically Substituted Dibenzyl Acyloins and their Use in the Synthesis of Fungus Pigments of the Pulvinone and Grevillin Types
Gill, Melvyn,Kiefel, Milton J.,Lally, Deborah A.,Ten, Abilio
, p. 1497 - 1518 (2007/10/02)
Dibenzyl acyloins including those bearing unsymetrically disposed aryl residues are assembled in high yield by reaction between the O-trimethylsilyl ethers of arylacetaldehyde cyanohydrins and benzyl Grignard reagents.These acyloins are deprotonated with
SYNTHESIS OF FUNGUS PIGMENTS OF THE GREVILLIN AND PULVINONE TYPES FROM BENZYLACYLOINS.
Gill, Melvyn,Kiefel, Milton J.
, p. 2085 - 2088 (2007/10/02)
Grevillin-B (2) and 3',4',4'-trihydroxypulvinone (3), principal colouring matters of the myorrhizal toadstool Suillus grevillei, are synthesised in good yield from a common precursor in the form of benzylacyloin 6.
SYNTHESIS OF GREVILLINS AND THEIR BIOGENETIC INTERRELATIONSHIP WITH TERPHENYLQUINONES, XYLERYTHRINS AND PULVINIC ACIDS
Pattenden, Gerald,Pegg, Neil A.,Kenyon, Ronald W.
, p. 4749 - 4752 (2007/10/02)
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).
