Investigation on the chemistry of berbans-VII. Synthesis of 10,11-dimethoxy(depyrrolo)raunescine stereoisomers

I. Tóth, L. Szabó, M. Kajtár-Peredi, E. Gács-Baitz, L. Radics, Cs Szántay

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Abstract

Acyloxy-ketone rearrangement, proceeding by the action of base, has been observed in the case of ketone 2. By the reduction of ketones 2 and 3 with sodium boron hydride, new 10, 11-dimethoxy(depyrrolo)raunescine stereoisomers (5a-7a) have been prepared. Previously known alcohols with alloberban skeleton (12,13) have been similarly converted into tetracyclic raunescine stereoisomers (8a,9) by the oxido-reductive method. The stereochemistry of these compounds has been investigated by physical (1H NMR, IR) and by chemical methods.

Original languageEnglish
Pages (from-to)2113-2122
Number of pages10
JournalTetrahedron
Volume34
Issue number14
DOIs
Publication statusPublished - 1978

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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