Sigurjónsson, SvanurHaraldsson, Gudmundur G.2025-11-202025-11-202024-01Sigurjónsson, S & Haraldsson, G G 2024, 'Asymmetric Synthesis of Methoxylated Ether Lipids : Total Synthesis of Polyunsaturated C18:3 Omega-3 and Omega-6 MEL Triene Derivatives', Molecules, vol. 29, no. 1, 223. https://doi.org/10.3390/molecules290102231420-304921821433492562019-90c1-4bce-b0dc-ee28ae222c8f8518187654638202806https://hdl.handle.net/20.500.11815/7490Publisher Copyright: © 2023 by the authors.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 center. 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 the synthesis of various types of MELs.1406955eninfo:eu-repo/semantics/openAccessasymmetric synthesismethoxylated ether lipid (MEL)semi-hydrogenationshark liver oilAnalytical ChemistryChemistry (miscellaneous)Molecular MedicinePharmaceutical ScienceDrug DiscoveryPhysical and Theoretical ChemistryOrganic Chemistry/dk/atira/pure/researchoutput/researchoutputtypes/contributiontojournal/article10.3390/molecules29010223