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Isolation of a novel oxygenated dimer of 3 methylindole 5a beta h 11a alpha h 12 beta hydroxy 10b beta 12 alpha dimethyl 5a 10b 11a 12 tetrahydro 6h oxazolo 3 2 a 4 5 b' diindole and structure determination of its acetylated derivative



Isolation of a novel oxygenated dimer of 3 methylindole 5a beta h 11a alpha h 12 beta hydroxy 10b beta 12 alpha dimethyl 5a 10b 11a 12 tetrahydro 6h oxazolo 3 2 a 4 5 b' diindole and structure determination of its acetylated derivative



Chemical and Pharmaceutical Bulletin 33(5): 1878-1888



A new oxygenated dimer of 3-methylindole was isolated from the reaction mixture obtained by oxygenation of 3-methylindole in the presence of a sterically crowded Co catalyst, N,N-(cis-1,2-cyclohexylene)bis(3-tert-butylsalicylideneaminato)cobalt(II). X-ray crystal structure determination of its acetylated derivative revealed it to be 6-acetyl-5a.beta.(H),11a.alpha.(H)-12.beta.-hydroxy-10b.beta.,12.alpha.-dimethyl-5a,10b,11a,12-tetrahydro-6H-oxazolo[3,2-a:4,5-b']diindole, with a novel C6-C4N-C3NO-C4N-C6 ring system. Two conformers due to restricted rotation of the acetyl group of the acetylated derivative was observed by temperature-dependent 1H-NMR-spectroscopy.

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