Asymmetric synthesis of γ-hydroxy α, β-unsaturated amides via an AD-elimination process; synthesis of (+)-Coriolic acid

Article abstract of DOI:10.1016/S0040-4039(00)60351-9

An efficient, asymmetric synthetic route to γ-hydroxy α,β-imsaturated ketone and/or aldehyde equivalents is described. Thus, 3,4-dihydroxy N-methoxy-N-methyl amides are treated in a one pot process with thionyl chloride followed by DBU to give the corresponding γ-hydroxy α,β-unsaturated amides in good yields. Based on this methodology, a short sequence leading to natural (+)-Coroilic acid is presented.