
TY  - JOUR
A1  - Caygill, Graham B. 
A1  - Larsen, David S. 
A1  - McFarlane, Brett S. 
T1  - Synthetic Approaches to the Angucycline Antibiotics: A Synthesis of (&#177;)-Hatomarubigin B and C.
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1997
VL  - 50
IS  - 4
SP  - 301
EP  - 308
KW  - 
UR  - https://doi.org/10.1071/C96106 
N2  - 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. 
ER  -

