
%0 Journal Article
%A Rozek, Tomas 
%A Rozek, Tomas 
%A Taylor, Dennis K. 
%A Taylor, Dennis K. 
%A Tiekink, Edward R. T. 
%A Tiekink, Edward R. T. 
%A Bowie, John H. 
%A Bowie, John H. 
%T Syntheses of Angucyclinones Related to Ochromycinone. III.  An 11-Hydroxy Isomer and Some Reduced Analogues
%J Australian Journal of Chemistry
%D 1999/02/19
%V 52
%N 2
%P 129-136
%K 
%R https://doi.org/10.1071/C98124
%U https://www.publish.csiro.au/paper/C98124 
%X The boron triacetate assisted Diels Alder reaction between racemic 5,5-dimethyl-3-vinylcyclohex- 2-enyl acetate and 5-hydroxynaphthoquinone yields the racemic 11-hydroxy-3,3-dimethyl-7,12-dioxo- 1,2,3,4,6,6a,7,12,12a,12b-decahydrobenzo&#91;a&#93;anthracen-1-yl acetate as the sole stereoisomer by regio- and stereo-selective cis endo addition. Aromatization of the Diels Alder adduct followed by hydrolysis of the acetate and oxidation of the resultant 1-hydroxy group gives the target angucyclinone, 11-hydroxy-3,3-dimethyl-1,2,3,4,7,12-hexahydrobenzo&#91;a&#93;anthracene-1,7,12-trione, in an overall yield of 37% from 5-hydroxynaphthoquinone. The regio- and stereo-selectivity of the Diels Alder addition is confirmed by a combination of 13C n.m.r. spectroscopy and X-ray crystallography. 
