Syntheses and stereochemical assignment of toxic C 17-polyacetylenic alcohols, virols A, B, and C, isolated from water hemlock (Cicuta virosa)

K Uwai, Y Oshima, T Sugihara, T Ohta

Index: Uwai, Koji; Oshima, Yoshiteru; Sugihara, Takumichi; Ohta, Tomihisa Tetrahedron, 1999 , vol. 55, # 31 p. 9469 - 9480

Full Text: HTML

Citation Number: 21

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 ...