Syntheses and stereochemical assignment of toxic C17-polyacetylenic alcohols, virols A, B, and C, isolated from water hemlock (Cicuta virosa)

Koji Uwai, Yoshiteru Oshima, Takumichi Sugihara, Tomihisa Ohta

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

In the course of our study on neurotoxic C17-polyacetylenic alcohols of the toxic plant, Cicuta virosa, virols A (1), B (2), and C (3) were synthesized by stereoselective routes to confirm their stereochemistry and to obtain supply of these compounds for pharmacological study. The syntheses used chiral 3-hydroxy-1-alkyne building blocks, Pd(0)CuI(I)-catalyzed coupling of acetylene with vinyl chloride, and heterocoupling reaction of acetylene mediated by CuI. As a result, the absolute configuration of the stereogenic center of virols A (1), B (2), and C (3) was confirmed as S, S, and S, respectively.

Original languageEnglish
Pages (from-to)9469-9480
Number of pages12
JournalTetrahedron
Volume55
Issue number31
DOIs
Publication statusPublished - 1999 Jul 30

Keywords

  • C-polyacetylenic alcohol
  • Cicuta virosa
  • Toxin

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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