Carminomycinone

Daunomycinone derivatives Demethylation Corresponding demethylated Carminomycinone derivatives Sepedonlum chrysospermum Beauveria sulfurescens... 

Selective methylation of a.,a a."-trihydroxyanthraquinones. Quinones of this type (e.g. 1) are mono-methylated by reaction with excess diazomethane in CH2CI2. This reaction can be used to convert carminomycinone into daunomycinone (3) in 45% yield. ... 

A-Glycosyl-1,2,3-triazoles, obtainable from glycosyl azides, were used for glycoside synthesis in TMSOTf-promoted reactions [577]. Thus, the reaction of 263 with carminomycinone 264 produced the glycoside 265 in excellent yield [577] (Scheme 4.51). 

Apart from its use as a valuable mordant dyestuff for textiles, cochineal (EEC 120) is still used as a colourant in cosmetics, foods, aperitif and beverages (ref. 194) and is one of the several permitted natural colourants which includes for example p-carotene, betanidin from Beta vulgaris, curcumin from Curcuma tonga, certain anthocyanins and chlorophyll complexes to quote a few structures. Commercial interest in natural products such as cochineal and carminic acid has been reactivated by the increasing pressures to avoid synthetic azo colours, their association with potential carcinogenic attributes and the increasing popularity of green issues. Carminic acid is reputed to possess some anticancer activity (ref. 195,196) and is a distant structural relative of the antibiotics, carminomycin and carminomycinone. 

Dideoxy-L-/> xo-hexopyranosyl-c-pyrromicinone and l-Aeoxy-n-erythro-pentopyranosyl-carminomycinone.-daunomycinone, and - -pyrromicinone have been prepared from the appropriate mycinone and glycosyl bromide by Koenigs-Knorr procedures. ... 

Carminomycinone has also been coupled with 3-azido-3-deoxy- and... 

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