The absolute configuration of (+)- and (−)-1-phenylundec-4-yn-3-ols. Synthesis of (R)-4-dodecanolide, a component of the defensive secretion of rove beetle Bledius mandibullaris

Hydrogenation of the triple bond of (+)-1-phenylundec-4-yn-3-ol (obtained from (+)-[η 6 -(3-hydroxyundec-4-yn-1-yl)benzene]chromium tricarbonyl) with the NaBH 4 -NiCl 2 ·6H 2 O reagent system in MeOH leads to (−)-1-phenylundecan-3-ol. Ozonolysis of the phenyl ring in the corresponding acetate gives ( R )-(−)-acetoxydodecanoic acid, lactonization of which leads to the known ( R )-(+)-4-dodecanolide. The starting (+)-1-phenylundec-4-yn-3-ol was thus shown to have the S -configuration.