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Asymmetric Synthesis of Methoxylated Ether Lipids: Total Synthesis of Polyunsaturated C18:3 Omega-3 and Omega-6 MEL Triene Derivatives.
- Source :
-
Molecules (Basel, Switzerland) [Molecules] 2023 Dec 31; Vol. 29 (1). Date of Electronic Publication: 2023 Dec 31. - Publication Year :
- 2023
-
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 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.
- Subjects :
- Glycerol
Ethyl Ethers
Ethers
Glyceryl Ethers
Ether
Fatty Acids, Omega-3
Subjects
Details
- Language :
- English
- ISSN :
- 1420-3049
- Volume :
- 29
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- Molecules (Basel, Switzerland)
- Publication Type :
- Academic Journal
- Accession number :
- 38202806
- Full Text :
- https://doi.org/10.3390/molecules29010223