Enantioselective synthesis of (-)-dendroprimine and isomers.
An enantioselective and diastereoselective synthesis of six 5,7-dimethylindolizidine isomers is described via an intramolecular cyclization that involves an allylsilyl nucleophilic group and an acyliminium ion. The first total synthesis of naturally occurring (-)-dendroprimine has been achieved in five steps.
De Saboulin Bollena
Axelle
A
Département de Chimie, UMR 6504, CNRS et Université Blaise Pascal (Clermont-Ferrand), 63177 Aubière, France.
Gelas-Mialhe
Yvonne
Y
Gramain
Jean-Claude
JC
Perret
Anne
A
Remuson
Roland
R
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D031667:Dendrobium / Q000737:chemistry; D006865:Hydrogenation; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D007212:Indolizines; C488243:dendroprimine