Tetrahedron p. 9469 - 9480 (1999)
Update date:2022-08-16
Topics:
Uwai, Koji
Oshima, Yoshiteru
Sugihara, Takumichi
Ohta, Tomihisa
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.
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