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Asymmetric Total Synthesis of 19,20-Epoxydocosapentaenoic Acid, a Bioactive Metabolite of Docosahexaenoic Acid.

ABSTRACT: In this study, we report the first asymmetric total synthesis of 19,20-epoxydocosapentaenoic acid (19,20-EDP), a naturally occurring bioactive cytochrome P450 metabolite of docosahexaenoic acid, a major constituent of fish oil. Our strategy involves direct asymmetric epoxidation to produce an enantiopure ?-epoxyaldehyde that can be appended to the rest of the skipped polyene core by Wittig condensation. Our route is step-economical and late divergent and could be an appealing method by which to synthesize EDP analogues for biological studies.

SUBMITTER: Cinelli MA

PROVIDER: S-EPMC7944941 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Asymmetric Total Synthesis of 19,20-Epoxydocosapentaenoic Acid, a Bioactive Metabolite of Docosahexaenoic Acid.

Cinelli Maris A MA Lee Kin Sing Stephen KSS

The Journal of organic chemistry 20191121 23

In this study, we report the first asymmetric total synthesis of 19,20-epoxydocosapentaenoic acid (19,20-EDP), a naturally occurring bioactive cytochrome P450 metabolite of docosahexaenoic acid, a major constituent of fish oil. Our strategy involves direct asymmetric epoxidation to produce an enantiopure <i>β</i>-epoxyaldehyde that can be appended to the rest of the skipped polyene core by Wittig condensation. Our route is step-economical and late divergent and could be an appealing method by wh ...[more]

PMID: 31701741

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