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Regiospecific synthesis of 1,4,5-trioxygenated anthraquinones. A total synthesis of islandicin

✍ Scribed by A.S. Kende; J.L. Belletire; E.L. Hume

Publisher
Elsevier Science
Year
1973
Tongue
French
Weight
191 KB
Volume
14
Category
Article
ISSN
0040-4039

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✦ Synopsis

This communication describes a solution to the general problem of the regiospecific synthesis of an unsymmetrically substituted anthraquinone system. Acetogenins containing this moiety are frequently encountered as antibiotics,' and the system is characteristic of the clinically important anthracyclines daunomycin J_ and adriamycin 2," as well as of the fungal metabolite islandicin 3 isolated by Raistrick from Penicillium islandicum.3 -2 R-OH Most anthraquinone syntheses have relied upon the Friedel-Crafts condensation of a phthalic anhydride with a suitable phenol derivative." With two unsymmetrical reactants, however, the orientation of the initial step may be ambiguous or may require the difficult separation of a mixture of structural isomers. Thus the reported synthesis of islandicin in 4.5% overall'yield from 2935

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