Enantioselective synthesis of methyl (5Z,8S)-8,9-epoxynon-5-enoate, an eicosanoid synthon |
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Authors: | M A Lapitskaya L L Vasiljeva K K Pivnitsky |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow, 119991, Russian Federation |
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Abstract: | A six-step synthesis of methyl (5Z,8S)-8,9-epoxynon-5-enoate, a known synthon of constanolactones and hepoxilins, from 5-hexynoic ester was developed. The enantiomeric
purity of the synthon was attained by S-enantiodirected dihydroxylation of a double bond in the intermediate methyl non-8-en-5-ynoate with subsequent enantioselective
hydrolysis of the epoxide group in the admixture of the minor R-enantiomer.
Dedicated to Academician V. A. Tartakovsky on his 75th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1586–1592, August, 2007. |
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Keywords: | constanolactones synthons asymmetric catalysis eicosanoids enantioselective synthesis oxiranes |
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