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Total Synthesis of (+)-(2S,3R)-Piscidic AcidviaCatalytic Asymmetric Dihydroxylation of a Trisubstituted Olefin

 

作者:

 

期刊: Bioscience, Biotechnology, and Biochemistry  (Taylor Available online 1999)
卷期: Volume 63, issue 5  

页码: 964-967

 

ISSN:0916-8451

 

年代: 1999

 

DOI:10.1271/bbb.63.964

 

出版商: Japan Society for Bioscience, Biotechnology, and Agrochemistry

 

关键词: piscidic acid;asymmetric dihydroxylation;catalytic asymmetric synthesis

 

数据来源: Taylor

 

摘要:

(+)-(2S,3R)-Piscidic acid was efficiently synthesized with high optical purity (90%e.e.)viaSharpless 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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