A novel enantioselective synthesis of (+)-biotin

Article abstract of DOI:10.1016/S0040-4039(00)77187-5

A conceptually attractive enantioselective 12-step synthesis of (+)-biotin from L-cysteine is reported based upon an intramolecular 1,3-dipolar cycloaddition sequence involving as key-steps (i) the macrothiolactonisation of acid 3 to Z-olefin (4), (ii) the thermolysis of the ene carbamoyl azide 5 in water with direct formation of a mixture of the benzylated derivative of (+)-biotin 6a and 6b.