Constitution, stereochemistry and conformational behaviour of the photoreaction product of 7-deacetoxy-7-oxokhivorin

Joseph I. Okogun, Helmut Duddeck, Gerhard Habermehl, Hans C. Krebs, Gábor Tóth, András Simon

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

By means of 2D NMR experiments (COSY, HMQC, HMBC, ROESY), the constitution of the photoreaction product 3-deoxo-1α,3 α-diacetoxy-1,2,3,3,8,30-hexahydro-18βH-andirobin (2), obtained by photolysis of 7-deacetoxy-7-oxokhivorin (1) in methanol, was shown to be a ring B seco-limonoid with the 14,15-epoxide intact. The configuration of C-8 is R. Ring C adopts a twist-boat conformation. No conformational preferences for the rotation of ring A in 2 with respect to rings C/D and for the side-chain C-6/C-7 could be detected. Nearly all 1H and all 13C resonances were assigned unambiguously.

Original languageEnglish
Pages (from-to)371-375
Number of pages5
JournalMagnetic Resonance in Chemistry
Volume36
Issue number5
DOIs
Publication statusPublished - May 1998

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Keywords

  • Boat conformation
  • C NMR
  • Conformational analysis
  • H NMR
  • H-detected ID gradient-selected long-range C, H correlation
  • Limonoids
  • NMR
  • ROESY
  • gs-COSY
  • gs-HMBC
  • gs-HMQC

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)

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