Abstract
In the course of our study on neurotoxic C 17-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.
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