title: Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (+/-)-hippodamine and (+/-)-epi-hippodamine.
abstract: BACKGROUND
  Hippodamine is a volatile defence alkaloid isolated from ladybird beetles which holds potential as an agrochemical agent and was the subject of a synthesis by our group in 2005.
  
  
  RESULTS
  Two enhancements to our previous syntheses of (+/-)-hippodamine and (+/-)-epi-hippodamine are presented which are able to shorten the syntheses by up to two steps.
  
  
  CONCLUSIONS
  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.
authors.affiliation: School of Chemistry, University of Nottingham, Nottingham NG7 2RD, UK. pcxan4@nottingham.ac.uk
authors.forename: Annabella F
authors.initials: AF
authors.lastname: Newton
authors.forename: Martin
authors.initials: M
authors.lastname: Rejzek
authors.forename: Marie-Lyne
authors.initials: ML
authors.lastname: Alcaraz
authors.forename: Robert A
authors.initials: RA
authors.lastname: Stockman