Toward a ‘reagent-free’ synthesis

Several synthetic pathways to cyclohex-5-ene-1R,2S,3R,4R-tetrol (conduritol C) and cyclohex-5-ene-1S,2R,3R,4R-tetrol (conduritol F) are compared; each is analyzed for effectiveness of waste minimization. The latest synthesis, reported in this manuscript, combines enzymatic transformations with electrochemical methods. The concept of “effective mass yield” (EMY) is defined and illustrated.