Asymmetric total synthesis of (-)-indicol by a carbene cyclization-cycloaddition cascade strategy.
The first total synthesis of a secodolastane, (-)-indicol, has been accomplished. The key reaction is a rhodium(II)-mediated carbene cyclization-cycloaddition cascade, by which the core bicyclo[5.4.0]undecane skeleton was assembled. In this one-pot reaction, a domino series of transformations resulting in the construction of three sigma bonds and three stereocenters was realized in good yield.
Lam
Sze Kui
SK
Department of Chemistry, and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, University of Hong Kong, Pokfulam Road, Hong Kong, PR China.
Chiu
Pauline
P
D001391:Azo Compounds / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D006838:Hydrocarbons / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
D001391:Azo Compounds; D004224:Diterpenes; D006838:Hydrocarbons; D007659:Ketones; C526637:indicol; C030011:carbene; D012428:Ruthenium; D008697:Methane