Stereocontrolled synthesis of four isomeric linoleate triols of relevance to skin barrier formation and function

Robert W Davis; Alexander Allweil; Jianhua Tian; Alan R Brash; Gary A Sulikowski

doi:10.1016/j.tetlet.2018.11.033

Stereocontrolled synthesis of four isomeric linoleate triols of relevance to skin barrier formation and function

Tetrahedron Lett. 2018 Dec 26;59(52):4571-4573. doi: 10.1016/j.tetlet.2018.11.033. Epub 2018 Nov 10.

Authors

Robert W Davis¹, Alexander Allweil¹, Jianhua Tian¹, Alan R Brash², Gary A Sulikowski^{1

2}

Affiliations

¹ Department of Chemistry, Institute of Chemical Biology, Vanderbilt University, Nashville, TN 37235, USA.
² Department of Pharmacology, Institute of Chemical Biology, Vanderbilt University, Nashville, TN 37232, USA.

Abstract

Linoleate triol esters are intermediates along the pathway of formation of the mammalian skin permeability barrier. In connection with the study of their involvement in barrier formation we required access to isomerically pure and defined samples of four linoleate triol esters. A common synthetic strategy was developed starting from isomeric alkynols derived from d-tartaric acid and 2-deoxy-d-ribose.

Keywords: Fatty acids; Stereochemistry; Synthesis strategy; Total synthesis.

Abstract

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