Journal of the Chemical Society. Perkin transactions I p. 823 - 830 (1992)
Update date:2022-08-23
Topics:
Mascal, Mark
Moody, Christopher J.
Slawin, Alexandra M. Z.
Williams, David J.
A stereospecific 7-step synthesis of (-)-indolactam V 1 from tryptophan methyl ester is described.The key steps are the photocyclisation of the dichloroamide 6 to give the isomeric 7-hydroxy-7-isopropylpyrrolo<4,3,2-fg><3>benzazocines 16 + 18 and the nitrene-mediated ring expansion of the derived azide 5 to give the 9-membered imine 4.The synthesis is completed by stereoselective reduction of the imine bond and N-methylation.
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