Copper(I)-mediated and microwave-assisted C(aryl)-O(carboxylic) coupling: synthesis of benzopyranones and isolamellarin alkaloids.
A simple and highly effective C-O(carboxylic) coupling reaction catalyzed by copper(I) salts has been developed to synthesize benzopyranones. The reaction of various 2-halobiarylcarboxylic acids was examined using microwave irradiation. A new class of pyrroloisoquinoline alkaloid, isolamellarin, was synthesized based on the annulation of dihydroisoquinoline with aryl pyruvates under basic condition and Cu-mediated/MW-assisted C-O(carboxylic) lactonization.
Thasana
Nopporn
N
Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Laksi, Bangkok, Thailand. nopporn@cri.or.th
Worayuthakarn
Rattana
R
Kradanrat
Phithakpong
P
Hohn
Elliot
E
Young
Lauren
L
Ruchirawat
Somsak
S
D000470:Alkaloids / Q000138:chemical synthesis*; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003374:Coumarins / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D006844:Hydrocarbons, Cyclic / Q000737:chemistry*; D008872:Microwaves; D008956:Models, Chemical
D000470:Alkaloids; D000970:Antineoplastic Agents; D002264:Carboxylic Acids; D003374:Coumarins; D006576:Heterocyclic Compounds, 4 or More Rings; D006844:Hydrocarbons, Cyclic; C489096:lamellarin alpha; D003300:Copper