3-(Acyloxy)-3-buten-2-ones as dienophiles in anthracyclinone synthesis. An efficient route to 4-demethoxy-7-deoxydaunomycinone derivatives

RJ Ardecky, D Dominguez…

Index: Ardecky, Robert J.; Dominguez, Domingo; Cava, Michael P. Journal of Organic Chemistry, 1982 , vol. 47, # 3 p. 409 - 412

Full Text: HTML

Citation Number: 24

Abstract

Biacetyl has been converted into a series of 3-(acyloxy)-3-buten-2-ones (13-17) which were characterized both spectroscopically and as their crystalline adducts with 1, 3- diphenylisobenzofuran. A comparative study has been made of the reaction of these dienophiles with three related transient anthraquinone-o-quinodimethanes (8) which are readily available from 2, 3-dimethylquinimin. The yield of tetracyclic adduct obtained is ...