The Willgerodt-Kindler reaction on lupenone: unusual oxidative dimerization.
In continuation of our interest in chemical modification of triterpenoids, the Willgerodt-Kindler reaction of a lupane type triterpenoid lupenone provided a novel dimerized product 2. Formation of 2 is associated with an unusual oxidative dimerization of lupenone under Willgerodt-Kindler reaction conditions. The structure 2 was confirmed by extensive analysis of spectroscopic data including ES-MS and 2D-NMR.
Biabani
Farooq
F
Medicinal Chemistry Division, Central Drug Research Institute, Lucknow, India. fbiabani@hotmail.com
Singh
Sanjay K
SK
Kumar
S
S
Raj
Kanwal
K
Pathak
A
A
D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D021241:Spectrometry, Mass, Electrospray Ionization; D014315:Triterpenes / Q000737:chemistry*; D000094042:Lupanes
D014315:Triterpenes; C470592:lupenone; D000094042:Lupanes