A-type cyclopentenone isoprostanoids are abundantly formed in vivo by radical peroxidation of eico- sapentaenoic 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 ␣rst 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 JuliaeKocienski reaction, and feature the semihydrogenation of an alkyne moiety for the installation of the labeled lower side chain.
First total synthesis of labeled EPA and DHA-derived A-type cyclopentenone isoprostanoids: [D2]-15-A3t-IsoP and [D2]-17-A4t-NeuroP
PORTA, ALESSIO;BRUNOLDI, ENRICO;ZANONI, GIUSEPPE;VIDARI, GIOVANNI
2014-01-01
Abstract
A-type cyclopentenone isoprostanoids are abundantly formed in vivo by radical peroxidation of eico- sapentaenoic 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 ␣rst 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 JuliaeKocienski reaction, and feature the semihydrogenation of an alkyne moiety for the installation of the labeled lower side chain.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
