Structural and stereochemical studies of a tetralin norsesquiterpenoid from Ligularia Kangtingensis

Guangbo Xie, Jin Tian, Katalin E. Kövér, Attila Mándi, Tibor Kurtán

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A chiral tetralin norsesquiterpenoid, ligukangtinol, was isolated from the plant Ligularia kangtingensis. Its planar structure was determined by extensive analysis of spectroscopic data (MS, IR, and NMR), and (1S,3R) absolute configuration of the tetralin ring was established by TDDFT-ECD calculations of the solution conformers. Conformational analysis and ECD calculations proved that the semiempirical helicity rules of 6-hydroxytetralins correlating the 1Lb Cotton effect and P/M helicity of the fused carbocyclic ring correctly predicts the absolute configuration and thus can be used for the configurational assignment of related substituted tetralin derivatives. Chirality 26:214-219, 2014.

Original languageEnglish
Pages (from-to)574-579
Number of pages6
JournalChirality
Volume26
Issue number9
DOIs
Publication statusPublished - Sep 2014

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Keywords

  • Ligularia kangtingensis
  • TDDFT-ECD calculation
  • chiral tetralin
  • inverse tetralin helicity rule
  • norsesquiterpenoid

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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