Fig. 5. Synthesis of 7-hydroxytriacontyl palmitate. Tetracosanal (10), as obtained from tetracosanoic acid through two redox steps, was added to the Grignard reagent 7a obtained from THP-protected, brominated 1,6-hexanediol (5). An acidic workup afforded 1,7-triacontanediol (11), which was then esterified with palmitoyl chloride to form 7-hydroxytriacontyl palmitate (12). Compounds in parentheses were not isolated, but used directly in the following step. Yields and procedural details are given in the Experimental section. Abbreviations: LAH = lithium aluminum hydride, DMAP = 4-dimethylaminopyridine.

Published as part of Busta, Lucas, Budke, Jessica M. & Jetter, Reinhard, 2016, Identification of b-hydroxy fatty acid esters and primary, secondary-alkanediol esters in cuticular waxes of the moss Funaria hygrometrica, pp. 38-49 in Phytochemistry 121 on page 44, DOI: 10.1016/j.phytochem.2015.10.007, http://zenodo.org/record/10485687