Reactions of indole derivatives with oxiranes and aziridines on silica. Synthesis of β-carbolin-1-one mimic of pancratistatin

Tomas Hudlicky, Uwe Rinner, Kevin J. Finn, Ion Ghiviriga

Research output: Contribution to journalArticle

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Abstract

(Chemical Equation Presented) Indole and several indoles functionalized at C-2 were condensed with oxiranes, vinyloxiranes, aziridines, and vinylaziridines in the solid state on the surface of silica. The yields of these reactions were compared to those obtained from Lewis acid-catalyzed ring-opening reactions performed in solution and found to be superior in each case. The solid-phase aziridine opening constituted a key step in the synthesis of the β-carbolin-1-one mimic of pancratistatin. Methyl 2-indolecarboxylate was found to react on the silica gel surface with N-tosylvinylaziridine in 68% yield. A nine-step synthesis of the pancratistatin mimic has been attained. The additional key transformation in this synthesis involved silica gel-catalyzed opening of an epoxide and hydrolysis of an acetonide. Detailed experimental procedures and full characterization are reported for all new compounds.

Original languageEnglish
Pages (from-to)3490-3499
Number of pages10
JournalJournal of Organic Chemistry
Volume70
Issue number9
DOIs
Publication statusPublished - Apr 29 2005

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Aziridines
Epoxy Compounds
Silicon Dioxide
Silica Gel
Derivatives
Indoles
Lewis Acids
Hydrolysis
pancratistatin
indole

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Reactions of indole derivatives with oxiranes and aziridines on silica. Synthesis of β-carbolin-1-one mimic of pancratistatin. / Hudlicky, Tomas; Rinner, Uwe; Finn, Kevin J.; Ghiviriga, Ion.

In: Journal of Organic Chemistry, Vol. 70, No. 9, 29.04.2005, p. 3490-3499.

Research output: Contribution to journalArticle

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