Synthesis of 2-(2-Hydroxyalkylidene)cyclopentanones and Their Bio-antimutagenic Activity

Abstract

2-(2-Hydroxyalkylidene)cyclopentanones (1) and 5-(2-hydroxyoctylidene)-2-cyclopentenone (2) were synthesized by the aldol reaction of cyclopentanone-enolate (3)/cyclopentenone-enolate (19) with 2-bromoalkanals (4)/2-bromooctanal (4c) and subsequent treatment of the products with sodium acetate. The stereochemistry of the condensation, substitution and elimination was elucidated. The bio-antimutagenic activity of 1 increased as the 2-hydroxyalkylidene group increased in length up to = CHCH(OH)C8H17.