Total Synthesis of (+)-(2S,3R)-Piscidic AcidviaCatalytic Asymmetric Dihydroxylation of a Trisubstituted Olefin
Bioscience Biotechnology and Biochemistry1999Vol. 63(5), pp. 964–967
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Abstract
(+)-(2S,3R)-Piscidic acid was efficiently synthesized with high optical purity (90% e.e.) via Sharpless catalytic asymmetric dihydroxylation of a trisubstituted olefin in only 6 steps from commercially available 4-hydroxyphenylpyruvic acid as the starting material. The reaction proceeded with high optical purity by using the chiral ligands, dihydroquinidine 2,5-diphenyl-4,6-pyrimidinediyl diether or dihydroquinidine 1,4-anthraquinonediyl diether.
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