کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5216066 1383251 2014 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
First total synthesis of labeled EPA and DHA-derived A-type cyclopentenone isoprostanoids: [D2]-15-A3t-IsoP and [D2]-17-A4t-NeuroP
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
First total synthesis of labeled EPA and DHA-derived A-type cyclopentenone isoprostanoids: [D2]-15-A3t-IsoP and [D2]-17-A4t-NeuroP
چکیده انگلیسی

A-type cyclopentenone isoprostanoids are abundantly formed in vivo by radical peroxidation of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), which are consumed daily for the prevention of cardiovascular and neurological pathologies. To facilitate in depth studies concerning the effects of these oxidized isoprostanoids on human health, labeled derivatives are necessary. In this paper, we have accomplished the first total synthesis of labeled A-type cyclopentenone isoprostanoids, namely 17,18-[D2]-15-A3t-IsoP and 19,20-[D2]-17-A4t-NeuroP. The two enantioselective routes are highly convergent, stemming from a common intermediate, readily available by a Julia-Kocienski reaction, and feature the semihydrogenation of an alkyne moiety for the installation of the labeled lower side chain.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 70, Issue 7, 18 February 2014, Pages 1484-1491
نویسندگان
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