1(4H)-Naphthalenones in Anthracyclinone Synthesis: A New Route for the Total Synthesis of (+/-)-Aklavinone

Article abstract of DOI:10.1021/jo00282a028

A brief route for total synthesis of (+/-)-aklavinone (1a), the aglycon of the anticancer antibiotic aclacinomycin (1b), is described.Key features of the synthesis are the development of a brief, efficient route to the 1(4H)-naphthalenone 11, which was used as a synthon for the A and B rings, and homologation of keto aldehyde 17 to the keto anthraquinone acetic ester 16 via the intermediacy of the ketene thioacetal 19.