1,4-Dimethoxynaphthalene-2-methyl (‘DIMON’), an oxidatively labile protecting group for synthesis of polyunsaturated lipids

Jay Tromans; Bian Zhang; Bernard T. Golding

doi:10.1039/D3CC04292H

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1,4-Dimethoxynaphthalene-2-methyl (‘DIMON’), an oxidatively labile protecting group for synthesis of polyunsaturated lipids†

Jay Tromans,^a Bian Zhang^b and Bernard T. Golding

*^a

Author affiliations

* Corresponding authors

^a School of Natural & Environmental Sciences – Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, UK
E-mail: bernard.golding@ncl.ac.uk

^b BiBerChem Research Ltd, The Biosphere, Draymans Way, Newcastle Helix, Newcastle upon Tyne, UK

Abstract

A new benzyl-type protecting group (1,4-dimethoxynaphthalene-2-methyl, ‘DIMON’) for hydroxyl functions can be selectively removed under oxidative conditions without damaging polyunsaturated fatty acyl groups. Its application is shown by the first synthesis of an ether (plasmanyl) phospholipid containing the docosa-(4Z,7Z,10Z,13Z,16Z,19Z)-hexaenoyl group.

This article is part of the themed collection: Celebrating the scientific accomplishments of RSC Fellows

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Article information

DOI: https://doi.org/10.1039/D3CC04292H
Article type: Communication
Submitted: 31 Aug 2023
Accepted: 16 Oct 2023
First published: 23 Oct 2023
This article is Open Access

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Chem. Commun., 2023,59, 13333-13335

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1,4-Dimethoxynaphthalene-2-methyl (‘DIMON’), an oxidatively labile protecting group for synthesis of polyunsaturated lipids

J. Tromans, B. Zhang and B. T. Golding, Chem. Commun., 2023, 59, 13333 DOI: 10.1039/D3CC04292H

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Chemical Communications

1,4-Dimethoxynaphthalene-2-methyl (‘DIMON’), an oxidatively labile protecting group for synthesis of polyunsaturated lipids†

Abstract

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1,4-Dimethoxynaphthalene-2-methyl (‘DIMON’), an oxidatively labile protecting group for synthesis of polyunsaturated lipids

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