106942-20-5Relevant articles and documents
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.
ADDITION OF ORGANOMAGNESIUM REAGENTS TO CYANOHYDRIN-O-SILYL ETHERS: AN EFFICIENT AND FLEXIBLE SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED ACYLOINS
Gill, Melvyn,Kiefel, Milton J.,Lally, Deborah A.
, p. 1933 - 1934 (2007/10/02)
Acyloins are prepared in high yields via reaction between Grignard reagents and O-trimethylsilyl ethers of aldehyde cyanohydrins: the method is particularly useful for the preparation of discrete acyloins in which the substituens are unsymmetrically dispo
