Synthesis of 8-aryl-substituted coumarins based on ring-closing metathesis and Suzuki-Miyaura coupling: synthesis of a furyl coumarin natural product from Galipea panamensis.
The synthesis of 7-methoxy-8-(4-methyl-3-furyl)-2H-chromen-2-one, a natural product with antileishmanial activity recently isolated from the plant Galipea panamensis, is described. The key step is a Suzuki-Miyaura coupling of a furan-3-boronic acid and an 8-halocoumarin, which is advantageously synthesized using a ring-closing metathesis reaction. Several non-natural analogues are also available along these lines.
Institut fuer Chemie (Organische Synthesechemie), Universitaet Potsdam, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam-Golm, Germany. bernd.schmidt@uni-potsdam.de
Bernd
B
Schmidt
Stefan
S
Krehl
Alexandra
A
Kelling
Uwe
U
Schilde
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D027821:Rutaceae / Q000737:chemistry*; D013237:Stereoisomerism
D001688:Biological Products; D003374:Coumarins; D009942:Organometallic Compounds