A Synthesis of the C6,C11-Dideoxyanthracyclinone Skeleton via Hassall Cyclization and Oxidative Desilylation

Article abstract of DOI:10.1021/jo00243a001

A sequence of regiocontrolled Diels-Alder reactions has been used to prepare 15.Oxygenation of the benzylic silane in the presence of a fluoride source introduces the C7 hydroxyl group (95percent).Further conversion to the nitrile 21 followed by base-induced Hassall cyclization and oxidation gives the anthraquinone 25.Deprotection can be effected, but attempts to prepare 28 result in low yields.The oxygenation can be extended to certain enol silanes, but protodesilylation is a serious side reaction.