
TY  - JOUR
A1  - Elix, JA 
A1  - Jenie, UA 
A1  - Parker, JL 
T1  - A Novel Synthesis of the Lichen Depsidones Divaronic Acid and Stenosporonic Acid, and the Biosynthetic Implications
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1987
VL  - 40
IS  - 8
SP  - 1451
EP  - 1464
KW  - 
UR  - https://doi.org/10.1071/CH9871451 
N2  - The depsidones divaronic acid (24) (8-hydroxy-3-methoxy-1,6-dipropyl-11- oxo -11H- dibenzo [ b,e ][1,4]dioxepin-7-carboxylic acid) and stenosporonic acid (25) (8-hydroxy-3-methoxy-6-pentyl-l-propyl-ll-oxo-l1H-dibenzo[ b,e ][1,4]dioxepin-7-carboxylic acid) have been prepared by unambiguous synthesis, and have been shown to cooccur with colensoic acid, atranorin and chloroatranorin in the lichen Paraparmelia mongaensis. The syntheses employed a novel biomimetic-type approach which involved a Smiles rearrangement of a precursor meta-depside in the key step. This rearrangement has important biosynthetic implications and may account for the natural occurrence of isostructural depside-depsidone pairs. 
ER  -

