244308-15-4Relevant articles and documents
Nickel-catalyzed cyclizations of enoate equivalents: Application to the synthesis of angular triquinanes
Seo, Jeongbeob,Fain, Helene,Blanc, Jean-Baptiste,Montgomery, John
, p. 6060 - 6065 (1999)
Unsaturated acyloxazolidinones and α'-silyloxy enones were found to be effective substrates in nickel-catalyzed organozinc-promoted cyclizations. Both groups served as convenient enoate equivalents, whereas methyl enoates themselves were inefficient substrates. A five-step procedure for the conversion of dimethylcyclopentenone into a highly functionalized angular triquinane was developed utilizing this observation. The key step of the procedure involves a nickel-catalyzed reductive cyclization/Dieckmann condensation sequence involving a cyclic enone tethered to an unsaturated acyloxazolidinone or α'-silyloxy enone. The method was applied in a formal synthesis of pentalenene, pentalenic acid, and deoxypentalenic acid.