A stereospecific 7-step synthesis of (–)- indolactam V1 from tryptophan methyl ester is described. The key steps are the photocyclisation of the dichloroamide 6 to give the isomeric 7-hydroxy-7-isopropyl-pyrrolo[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.
M. Mascal, C. J. Moody, A. M. Z. Slawin and D. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1992, 823 DOI: 10.1039/P19920000823
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