17241-40-6Relevant articles and documents
Regiospecific Reactions of Some Vinylogous Ketene Acetals with Haloquinones and Their Regioselective Formation by Dienolization
Brisson, Clement,Brassard, Paul
, p. 1810 - 1814 (1981)
Regiospecific reactions of simple 1,3-bis(trimethylsiloxy)-1,3-butadienes with 2,5- and 2,6-dichlorobenzoquinones gave chloronaphthoquinones which, by applying the appropriate vinylketene acetal, provided various monomethyl ethers of isomeric polyhydroxyanthraquinones.The first total synthesis of macrosporin (27) was obtained in this way and the proposed structure for "cajaquinone" (28) found to be incorrect.Simple syntheses of 2-hydroxy-3-methylanthraquinone (16), phomarin (19), soranjidiol (22) and other naturally occuring quinones are also described.The dienolization of 1-methoxy-2,4-pentanedione in the presence of chlorotrimethylsilane gave either 1- or 5-methoxy-2,4-bis(trimethylsiloxy)-1,3-pentadiene, depending upon the reaction conditions.Both dienes react with haloquinones, giving regiospecific products, e.g., tetra-O-methylerythrolaccin (35).
About the synthesis of some digitalis anthraquinones
Imre,Ersoy
, p. 592 - 593 (2007/10/13)
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