Absolute stereochemistry of cicutoxin and related toxic polyacetylenic alcohols from Cicuta virosa

Tomihisa Ohta, Koji Uwai, Rikako Kikuchi, Shigeo Nozoe, Yoshiteru Oshima, Kenrou Sasakl, Fumihiko Yoshizaki

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

The absolute stereostructures of cicutoxin (1) and related toxic polyacetylenic alcohols, isocicutoxin (2), and virols A (3) and C (4), from Cicuta virosa ware determined on the basis of spectroscopic analysis. The CD exciton chirality method was successfully applied to 4-methoxybenzoates of diyne-conjugated polyenyl alcohol systems. Fatal doses of these compounds on mice are also reported.

Original languageEnglish
Pages (from-to)12087-12098
Number of pages12
JournalTetrahedron
Volume55
Issue number41
DOIs
Publication statusPublished - 1999 Oct 8

Keywords

  • Optical properties
  • Polyacetylenic alcohols
  • Stereochemistry

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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