Enantiospecific Synthesis of (-)-Tabtoxinine &β-Lactam

Article abstract of DOI:10.1021/jo00027a024

A convergent, 10-step synthesis of optically active tabtoxinine β-lactam <(-)-1> has been described.Key features of the synthetic route include (1) preparation of a new γ-cation amino acid synthon, (-)-4, and its use as an electrophile (3 -> 11); (2) the one-pot conversion of methyl sulfide 11 to the Cbz-protected amine 12 via stereoselective sulfilimine rearrangement; and (3) chemoselective lactone ring opening in spiro lactam 15a.Synthons (-)-4 and 3 are available on a semipreparative scale.