Synthesis of (-)-indolactam V

Mark Mascal, Christopher J. Moody, Alexandra M Z Slawin, David J. Williams

Research output: Contribution to journalArticle

45 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)823-830
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number7
StatePublished - 1992
Externally publishedYes

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Imines
Methylation
Azides
indolactam V
phenylnitrene
tryptophan methyl ester

ASJC Scopus subject areas

  • Chemistry(all)

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.

Synthesis of (-)-indolactam V. / Mascal, Mark; Moody, Christopher J.; Slawin, Alexandra M Z; Williams, David J.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 7, 1992, p. 823-830.

Research output: Contribution to journalArticle

Mascal, M, Moody, CJ, Slawin, AMZ & Williams, DJ 1992, 'Synthesis of (-)-indolactam V', Journal of the Chemical Society, Perkin Transactions 1, no. 7, pp. 823-830.
Mascal M, Moody CJ, Slawin AMZ, Williams DJ. Synthesis of (-)-indolactam V. Journal of the Chemical Society, Perkin Transactions 1. 1992;(7):823-830.
Mascal, Mark ; Moody, Christopher J. ; Slawin, Alexandra M Z ; Williams, David J. / Synthesis of (-)-indolactam V. In: Journal of the Chemical Society, Perkin Transactions 1. 1992 ; No. 7. pp. 823-830.
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