Abstract
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-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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 823-830 |
| Number of pages | 8 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| Issue number | 7 |
| State | Published - 1992 |
| Externally published | Yes |
ASJC Scopus subject areas
- Chemistry(all)
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Cite this
Mascal, M., Moody, C. J., Slawin, A. M. Z., & Williams, D. J. (1992). Synthesis of (-)-indolactam V. Journal of the Chemical Society, Perkin Transactions 1, (7), 823-830.