Stereoselective introduction of oxygen functionalities at the 11β- position of erythrinan skeleton: Total syntheses of (±)-erythristemine and (+)-erythrartine

Article abstract of DOI:10.1248/cpb.42.197

Oxidation of 8-oxoerythrinan and 8-oxo-1,7-cycloerythrinan derivatives with 2 mol eq of ceric ammonium nitrate in alcohols or acetic acid gave the corresponding 11β-alkoxy or acetoxy compounds in moderate yield. Thus, (±)- 3,3,15,16-tetramethoxy-1,7-cycloerythrinan-2,8-dione and (+)-erysotramidine gave the corresponding 11β-methoxy and 11β-acetoxy derivatives on oxidation in methanol and in acetic acid, respectively. Those compounds were respectively converted into (±)-erythristemine and (+)-erythrartine in several steps, thus achieving the total synthesis of these alkaloids.

Full text of DOI:10.1248/cpb.42.197

NII-Electronic Library Service

NII-Electronic Library Service

NII-Electronic Library Service

NII-Electronic Library Service

NII-Electronic Library Service

NII-Electronic Library Service

NII-Electronic Library Service