Work

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

Year: 2019

Type: article

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 β -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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.9b02378

Authors: Maris A. Cinelli, Kin Sing Stephen Lee

Institution: Michigan State University

Language: English

Topic: Fatty Acid Research and Health

Subfield: Nutrition and Dietetics

Field: Nursing

Domain: Health Sciences

Open Access status: green

Funders: National Institute of Environmental Health Sciences, Division of Mathematical Sciences

Awards: G1088101296, G2062977162, Identifying the receptors of environmentally sensitive epoxy-eicosanoids with AMS