Radical addition reactions to allylstannanes having substituents at C-1. Highly efficient synthesis of enantiomerically pure α-alkylcyclopentenones, the key component for synthesis of prostaglandins by the two-component coupling process

Article abstract of DOI:10.1021/jo00100a010

A highly efficient and practical method for the synthesis of enantiomerically pure 4-alkoxy-2-alkyl-2-cyclopenten-1-ones 1, the key component for the preparation of prostaglandins via the two-component coupling process, has been developed. The method involves the preparation of 4-alkoxy-2-methylene-3-(tributylstannyl)cyclopentan-1-one 6 from readily available 4-alkoxy-2[(diethylamino)methyl]-2-cyclopenten-1-one 5 and its reaction with alkyl radicals.