Syntheses and Stereochemical Assignment of Toxic C_(17)-Polyacetylenic Alcohols, Virols A,B,and C,Isolated from Water Hemlock (Cicuta virosa)

摘要

In the course of our study on neurotoxic C_(17)-polyacetlylenic alcohols of the toxic plant, Cicuta virosa, virols A(1),B(2),and C(3) were synthesized by stercoselective routes to confirm their stereochemistry and to obtain supply of these compounds for pharmacological study. The syntheses used chiral 3-hydroxy-1-alkyne buklding blocks, Pd(0)-CuI(I)-catalyzed coupling of acetylene with vinyl chloride, and heterocoupling reactionof acetylene mediated by CuI. As a result, the absolute configurationof the stereogenic center of virols A(1),B(2),C(3),and C(3) was confirmed as S,S,and S,tespectively.