Synthesis of unsymmetrical benzil licoagrodione.
A synthesis of unsymmetrical 1,2-diarylethane-1,2-dione is reported involving the intramolecular cyclization of anionic benzylic ester of the aryl benzyl ether followed by oxidation employing dioxirane. With the use of microwave irradiation, licoagrodione was prepared from Claisen rearrangement of the corresponding allyl phenyl ether 1,2-diketone readily available from the Lindlar's reduction of the corresponding alkyne derivative. Subsequent removal of protecting groups then furnished the desired product.
Worayuthakarn
Rattana
R
Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Laksi, Bangkok 10210, Thailand.
Boonya-udtayan
Sasiwadee
S
Arom-oon
Eakarat
E
Ploypradith
Poonsakdi
P
Ruchirawat
Somsak
S
Thasana
Nopporn
N
D003500:Cyclization; D006037:Glyoxal / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000528:radiation effects; D008872:Microwaves; D015394:Molecular Structure; D010658:Phenylglyoxal / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000528:radiation effects; D013237:Stereoisomerism
C532794:licoagrodione; D006037:Glyoxal; D010658:Phenylglyoxal; C006697:benzil