TY - JOUR
T1 - Syntheses and stereochemical assignment of toxic C17-polyacetylenic alcohols, virols A, B, and C, isolated from water hemlock (Cicuta virosa)
AU - Uwai, Koji
AU - Oshima, Yoshiteru
AU - Sugihara, Takumichi
AU - Ohta, Tomihisa
PY - 1999/7/30
Y1 - 1999/7/30
N2 - 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.
AB - 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.
KW - C-polyacetylenic alcohol
KW - Cicuta virosa
KW - Toxin
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U2 - 10.1016/S0040-4020(99)00520-7
DO - 10.1016/S0040-4020(99)00520-7
M3 - Article
AN - SCOPUS:0033618469
VL - 55
SP - 9469
EP - 9480
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 31
ER -