First enantioselective total synthesis of (-)-tejedine.
[structure: see text] The first enantioselective total synthesis of (-)-tejedine (1) is reported. Tejedine is a seco-bisbenzyltetrahydroisoquinoline isolated in 1998 as a minor component from Berberis vulgaris. The synthesis was achieved using a strategy employing four key steps, including a chiral auxiliary-assisted diastereoselective Bischler-Napieralski cyclization.
Wang
You-Chu
YC
Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland and Labrador, Canada A1B 3X7.
Georghiou
Paris E
PE
D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D013237:Stereoisomerism; D014961:X-Ray Diffraction
D007546:Isoquinolines; C465249:tejedine