1 (4H)-Naphthalenones in anthracyclinone synthesis: a new route for the total synthesis of (.+-.)-aklavinone

FM Hauser, P Hewawasam, YS Rho

Index: Hauser, Frank M.; Hewawasam, Piyasena; Rho, Young S. Journal of Organic Chemistry, 1989 , vol. 54, # 21 p. 5110 - 5114

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Citation Number: 24

Abstract

A brief route for total synthesis of (&)-aklavinone (la), the aglycon of the anticancer antibiotic aclacinomycin (lb), is described. Key features of the synthesis are the development of a brief, efficient route to the l (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.