
%0 Journal Article
%A Caygill, Graham B. 
%A Larsen, David S. 
%A McFarlane, Brett S. 
%T Synthetic Approaches to the Angucycline Antibiotics: A Synthesis of (&#177;)-Hatomarubigin B and C.
%J Australian Journal of Chemistry
%D 1997/06/30
%V 50
%N 4
%P 301-308
%K 
%R https://doi.org/10.1071/C96106
%U https://www.publish.csiro.au/paper/C96106 
%X The synthesis of the angucycline natural products hatomarubigin B and C in racemic form is described. The key step in the construction of the benz&#91;a&#93;anthraquinone skeleton of these molecules was the Diels&#8211;Alder reaction of the acetate of (E,1R*,5R*)-3-(2&#8242;-methoxyvinyl)-5-methylcyclohex-2-en-1-ol and 5-acetoxy-8-hydroxy-1,4-naphthoquinone. Methylation of the C11 phenolic group of the resulting cycloadduct, followed by aromatization of the B ring with subsequent deacylation gave (&#177;)-hatomarubigin C. Oxidation of the latter compound with Dess-Martin periodinane, 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one, gave (&#177;)-hatomarubigin B. 
