Total synthesis of 11-deoxydaunomycinone and analogs by a tandem Claisen-Diels-Alder strategyThe Journal of Organic Chemistry
Publication VersionPublished Version
Abstract11-Deoxydaunomycinone (6), ita 4-deoxy analogue 5, and 1-methoxy-4,ll-dideoxyduanomycinone were prepared by a sequence involving an intramolecular acyl transfer reaction followed by a tandem Claisen-Diels-Alder reaction. The resulting diketone could be oxidized to naphthoquinone 11 with DDQ. This quinone was then treated with either 1-[ (trimethylsilyl)oxy]butadiene or l-methoxy-1,3-cyclohexadiene to provide adducts that could be transformed into 5 and 6. Unfortunately, the presence of the C-7 carbonyl group decreased the regioselectivity of 11 in Diels-Alder reactions.
Copyright OwnerAmerican Chemical Society
Citation InformationGeorge A. Kraus and Soon Hyung Woo. "Total synthesis of 11-deoxydaunomycinone and analogs by a tandem Claisen-Diels-Alder strategy" The Journal of Organic Chemistry Vol. 52 Iss. 22 (1987) p. 4841 - 4846
Available at: http://works.bepress.com/george_kraus/215/