Total synthesis of (+)-lepadin B: stereoselective synthesis of nonracemic polysubstituted hydroquinolines using an RC-ROM process.
This communication describes a new tandem metathesis reaction for which an RC-ROM mechanism was experimentally supported. This process was successfully applied to the synthesis of cis-fused polyhydroquinolines enabling a short stereoselective total synthesis of ent-lepadin B.
Barbe
Guillaume
G
Département de chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
Charette
André B
AB
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D008968:Molecular Conformation; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D011804:Quinolines; C414923:lepadin B