Stereoselective formal synthesis of (−)-mesembrane by intramolecular condensation of chiral amide and 1,3-cyclohexanedione moiety

A new stereoselective formal synthesis of (−)-mesembrane has been achieved by intramolecular condensation of chiral amide and 1,3-cyclohexanedione moiety. The precursor amide was readily prepared by condensation of the corresponding chiral amine and acid. Condensation provided moderate ratios of ene-amide derivatives and the following transformation of functional groups has yielded the known precursor for (−)-mesembrane, resulting in formal synthesis.