Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Asymmetric synthesis of methoxylated ether lipids: Total synthesis of polyunsaturated C18:3 omega-3 and omega-6 MEL triene derivatives

Version 1 : Received: 13 December 2023 / Approved: 13 December 2023 / Online: 14 December 2023 (01:42:46 CET)

A peer-reviewed article of this Preprint also exists.

Sigurjónsson, S.; Haraldsson, G.G. Asymmetric Synthesis of Methoxylated Ether Lipids: Total Synthesis of Polyunsaturated C18:3 Omega-3 and Omega-6 MEL Triene Derivatives. Molecules 2024, 29, 223. Sigurjónsson, S.; Haraldsson, G.G. Asymmetric Synthesis of Methoxylated Ether Lipids: Total Synthesis of Polyunsaturated C18:3 Omega-3 and Omega-6 MEL Triene Derivatives. Molecules 2024, 29, 223.

Abstract

The asymmetric synthesis of polyunsaturated triene C18:3 n-3 and C18:3 n-6 methoxylated ether lipids (MEL) of the 1-O-alkyl-sn-glycerol type is described as possible structural candidates for a triene C18:3 MEL of an unknown identity found in a mixture of shark and dogfish liver oil. Their C18:3 hydrocarbon chains constitute an all-cis methylene skipped n-3 or n-6 triene framework, along with a methoxyl group at the 2'-position and R-configuration of the resulting stereogenic centre. The methoxylated polyenes are attached by an ether linkage to the pro-S hydroxymethyl group of the glycerol backbone. The syntheses were based on the polyacetylene approach that involves a semi-hydrogenation of the resulting triynes. Both syntheses were started from our previously described enantio- and diastereomerically pure isopropylidene-protected glyceryl glycidyl ether, a double-C3 building block that was designed as a head group synthon for synthesis of various types of MELs.

Keywords

asymmetric synthesis; methoxylated ether lipid (MEL); semi-hydrogenation; shark liver oil

Subject

Chemistry and Materials Science, Organic Chemistry

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