Synthesis of (+)-coronafacic acid.
An enantioselective synthesis of (+)-coronafacic acid has been achieved. Rhodium-catalyzed cyclization of an alpha-diazoester provided the intermediate cyclopentanone in high enantiomeric purity. Subsequent Fe-mediated cyclocarbonylation of a derived alkenyl cyclopropane gave a bicyclic enone that then was hydrogenated and carried on to the natural product.
Taber
Douglass F
DF
Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
Sheth
Ritesh B
RB
Tian
Weiwei
W
D001688:Biological Products / Q000138:chemical synthesis; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes; D006865:Hydrogenation; D007192:Indenes / Q000138:chemical synthesis*; D012238:Rhodium; D013237:Stereoisomerism
D001688:Biological Products; D003517:Cyclopentanes; D007192:Indenes; C007201:cyclopentanone; C084266:coronafacic acid; D012238:Rhodium