Easy access to fully functionalized chiral tetrahydro-β-carboline alkaloids.
Takayoshi Arai, Makiko Wasai, Naota Yokoyama
Index: J. Org. Chem. 76(8) , 2909-12, (2011)
Full Text: HTML
Abstract
A four-step synthetic route to fully substituted chiral tetrahydro-β-carbolines (THBCs) is described. Starting from the (R,S,S)-Friedel-Crafts/Henry adduct obtained from three-component coupling of an indole, nitroalkene, and aldehyde catalyzed by imidazoline-aminophenol-CuOTf, the (1S,3S,4R)-THBCs were readily synthesized in a three-step operation including reduction of the nitro-functionality and Pictet-Spengler cyclization.
Related Compounds
Related Articles:
2008-11-07
[J. Chromatogr. A. 1210(1) , 115-20, (2008)]
Biosynthetic gene cluster for the cladoniamides, bis-indoles with a rearranged scaffold.
2011-01-01
[PLoS ONE 6(8) , e23694, (2011)]
2011-08-01
[Eur. J. Med. Chem. 46 , 3237-49, (2011)]
Interaction of β-carboline alkaloids with RNA.
2010-12-01
[DNA Cell. Biol. 29 , 753-761, (2010)]
Beta-carboline alkaloids bind DNA.
2010-08-02
[J. Photochem. Photobiol. B, Biol. 100 , 84-91, (2010)]