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

Research output: Contribution to journalArticle

4 Citations (Scopus)

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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Stereoisomerism
Ketones
Boranes
Stereochemistry
Skeleton
Sodium
Alcohols
Nuclear magnetic resonance

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Investigation on the chemistry of berbans-VII. Synthesis of 10,11-dimethoxy(depyrrolo)raunescine stereoisomers. / Tóth, I.; Szabó, L.; Kajtár-Peredi, M.; Gács-Baitz, E.; Radics, L.; Szántay, Cs.

In: Tetrahedron, Vol. 34, No. 14, 1978, p. 2113-2122.

Research output: Contribution to journalArticle

Tóth, I. ; Szabó, L. ; Kajtár-Peredi, M. ; Gács-Baitz, E. ; Radics, L. ; Szántay, Cs. / Investigation on the chemistry of berbans-VII. Synthesis of 10,11-dimethoxy(depyrrolo)raunescine stereoisomers. In: Tetrahedron. 1978 ; Vol. 34, No. 14. pp. 2113-2122.
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AU - Gács-Baitz, E.

AU - Radics, L.

AU - Szántay, Cs

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