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Study on the NBS-Induced Rearrangement of 2--Prenyltryptamines

Treatment of 2- tert -prenyltryptamines with N -bromosuccinimide gives clean access to the marine natural product flustramine C and analogues with the tert -prenyl group shifted to the 3a-position of the resulting pyrrolo[2,3- b ]indole (70-80%). Dihydroflustramine C was obtained by DIBAL-H reductio... Full description

Journal Title: Synthesis 2010, Issue 13, pp.2161-2170
Main Author: Lindel, Thomas
Other Authors: Adla, Santosh, Kumar , Golz, Gregor, G , Jones, Peter, G
Format: Electronic Article Electronic Article
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ID: ISSN: 0039-7881 ; E-ISSN: 1437-210X ; DOI: 10.1055/s-0029-1218811
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recordid: thieme_articles10.1055/s-0029-1218811
title: Study on the NBS-Induced Rearrangement of 2--Prenyltryptamines
format: Article
creator:
  • Lindel, Thomas
  • Adla, Santosh, Kumar
  • Golz, Gregor, G
  • Jones, Peter, G
subjects:
  • Alkaloids
  • Flustramines
  • Indole
  • Marine Natural Products
  • Prenyl Migration
ispartof: Synthesis, 2010, Issue 13, pp.2161-2170
description: Treatment of 2- tert -prenyltryptamines with N -bromosuccinimide gives clean access to the marine natural product flustramine C and analogues with the tert -prenyl group shifted to the 3a-position of the resulting pyrrolo[2,3- b ]indole (70-80%). Dihydroflustramine C was obtained by DIBAL-H reduction of flustramine C. Bromination or N-methylation of the indole moiety does not influence the course of the rearrangement.
language:
source:
identifier: ISSN: 0039-7881 ; E-ISSN: 1437-210X ; DOI: 10.1055/s-0029-1218811
fulltext: fulltext
issn:
  • 0039-7881
  • 00397881
  • 1437-210X
  • 1437210X
url: Link


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titleStudy on the NBS-Induced Rearrangement of 2--Prenyltryptamines
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subjectAlkaloids ; Flustramines ; Indole ; Marine Natural Products ; Prenyl Migration
descriptionTreatment of 2- tert -prenyltryptamines with N -bromosuccinimide gives clean access to the marine natural product flustramine C and analogues with the tert -prenyl group shifted to the 3a-position of the resulting pyrrolo[2,3- b ]indole (70-80%). Dihydroflustramine C was obtained by DIBAL-H reduction of flustramine C. Bromination or N-methylation of the indole moiety does not influence the course of the rearrangement.
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descriptionTreatment of 2- tert -prenyltryptamines with N -bromosuccinimide gives clean access to the marine natural product flustramine C and analogues with the tert -prenyl group shifted to the 3a-position of the resulting pyrrolo[2,3- b ]indole (70-80%). Dihydroflustramine C was obtained by DIBAL-H reduction of flustramine C. Bromination or N-methylation of the indole moiety does not influence the course of the rearrangement.
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abstractTreatment of 2- tert -prenyltryptamines with N -bromosuccinimide gives clean access to the marine natural product flustramine C and analogues with the tert -prenyl group shifted to the 3a-position of the resulting pyrrolo[2,3- b ]indole (70-80%). Dihydroflustramine C was obtained by DIBAL-H reduction of flustramine C. Bromination or N-methylation of the indole moiety does not influence the course of the rearrangement.
pub© Georg Thieme Verlag Stuttgart ˙ New York
doi10.1055/s-0029-1218811
volume2010
pages2161-2170