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

Article abstract of DOI:10.1007/s11172-013-0294-8

Hydrogenation of the triple bond of (+)-1-phenylundec-4-yn-3-ol (obtained from (+)[η⁶ (3-hydroxyundec-4-yn-1-yl)benzene]chromium tricarbonyl) with the NaBH₄-NiCl₂?6H₂O 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)-(+)-4dodecanolide. The starting (+)-1phenylundec-4-yn-3-ol was thus shown to have the Sconfiguration.