Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (+/-)-hippodamine and (+/-)-epi-hippodamine.

Key advances include a two-directional homologation by cross metathesis and a new tandem reductive amination/double intramolecular Michael addition which generates 6 new bonds, 2 stereogenic centres and two rings, giving a single diastereomer in 74% yield.