A Practical Synthesis of (+)-Biotin through Palladium Hydroxide on Charcoal-catalyzed Fukuyama Coupling Reaction

Abstract

The Fukuyama coupling reaction of thiolactone (2) with 5-ethoxy-5-oxopentylzinc iodide (4) in the presence of 0.65 mol% of non pyrophoric palladium hydroxide on charcoal (Pearlman's catalyst) provided a vinyl sulfide (3) carrying a C-4 side chain of (+)-biotin (1) in 87% yield.