Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (+/-)-hippodamine and (+/-)-epi-hippodamine.
Beilstein J Org Chem
; 4: 4, 2008 Jan 17.
Article
em En
| MEDLINE
| ID: mdl-18201377
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.CONCLUSION:
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.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Beilstein J Org Chem
Ano de publicação:
2008
Tipo de documento:
Article
País de afiliação:
Reino Unido