Stereocontrolled synthesis of four isomeric linoleate triols of relevance to skin barrier formation and function. Issue 52 (26th December 2018)

• Record Type: Journal Article
• Authors: Davis, Robert W.; Allweil, Alexander; Tian, Jianhua; Brash, Alan R.; Sulikowski, Gary A.
• Is Part Of: Tetrahedron letters. Volume 59:Issue 52(2018)
• Page Start: 4571
• Page End: 4573
• Publication Date: 2018-12-26
• Subjects: Total synthesis -- Stereochemistry -- Fatty acids -- Synthesis strategy; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.11.033
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Lipids. Chiral pool. Mosher Esters. Stereoselective. 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 fromd -tartaric acid and 2-deoxy-d -ribose.