Total synthesis of (-)-conocarpan and assignment of the absolute configuration by chemical methods.
(-)-Conocarpan (1) was synthesized by a method based on radical cyclization, and the absolute configuration was established by chemical degradation; the original 2R,3R-assignment to (+)-conocarpan should be reversed, as suggested by a later chiroptical study of model 2,3-dihydrobenzofurans.
Clive
Derrick L J
DL
Chemistry Department, University of Alberta, Edmonton, Alberta, CanadaT6G 2G2. derrick.clive@ualberta.ca
Stoffman
Elia J L
EJ
D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D001572:Benzofurans; D005663:Furans; C447284:conocarpan; C043168:coumaran