A photochemical entry to depsides: synthesis of gustastatin.
Herein, we propose a modular and general strategy to construct orcinol-type depsides based on the photolysis of functionalized benzodioxinones (I). Notably, resorcinylic esters are obtained without competing isocoumarin (II) formation, exemplified by the first total synthesis of gustastatin in 10 steps from commercially available trihydroxybenzoic acid. [Structure: see text]
García-Fortanet
Jorge
J
Department of Biochemistry, University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Blvd., Dallas, TX 75390-9038, USA.
Debergh
John R
JR
De Brabander
Jef K
JK
D007202:Indicators and Reagents; D029562:Magnoliaceae / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification
D007202:Indicators and Reagents; D010636:Phenols; C488055:gustastatin