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

✍ Scribed by Le Anh Tuan; Guncheol Kim

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 484 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.02.136

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✦ Synopsis

A new stereoselective formal synthesis of (À)-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 (À)-mesembrane, resulting in formal synthesis.

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