Journal or Book Title
The Journal of Organic Chemistry
11-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.
American Chemical Society
Kraus, George A. and Woo, Soon Hyung, "Total synthesis of 11-deoxydaunomycinone and analogs by a tandem Claisen-Diels-Alder strategy" (1987). Chemistry Publications. 677.