Efficient synthetic approaches to the common scaffold of indole alkaloids.
Birch reductive alkylation of 2-aminobiphenyls affords access to highly functionalized polyenes that react through a Pd(II)-catalyzed oxidative amination cascade or through a double 1,4-addition process to provide the tetracyclic skeleton of indole alkaloids with up to four stereogenic centers created in a single-pot operation.
Beniazza
Redouane
R
Université Bordeaux 1, Institut des Sciences Moléculaires, UMR-CNRS 5255, 351, Cours de la libération, F-33405 Talence cedex, France.
Dunet
Julie
J
Robert
Frédéric
F
Schenk
Kurt
K
Landais
Yannick
Y
D000085:Acetates / Q000737:chemistry; D000478:Alkylation; D000586:Amination; D018360:Crystallography, X-Ray; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry