期刊
CHEMISTRY AND PHYSICS OF LIPIDS
卷 156, 期 1-2, 页码 41-44出版社
ELSEVIER IRELAND LTD
DOI: 10.1016/j.chemphyslip.2008.07.013
关键词
Dimethylene interrupted fatty acids; Methoxylated fatty acids; 5,9-Octadecadienoic acids; Synthesis; Sponges
资金
- National Institutes of Health [S06GM08102]
The first total synthesis for the sponge derived (5Z,9Z)-(+/-)-2-methoxy-5,9-octadecadienoic acid, an analog of taxoleic acid, was accomplished in seven steps and in a 10% overall yield. It was again corroborated that the best strategy to prepare these cis,cis dimethylene interrupted double bonds is the double-alkyne bromide coupling reaction of 1,5-hexadiyne, which provides the advantage of achieving a 100% cis stereochemical purity for both double bonds after hydrogenation under Lindlar conditions. The alpha-methoxy functionality was best prepared via the Mukaiyama reaction of (4Z,8Z)-heptadecadienal with trimethylsilyl cyanide and triethylamine followed by acid hydrolysis. Selective methylation of the hydroxyl group of (5Z,9Z)-(+/-)-2-hydroxy-5,9-octadecadienoic acid was achieved with sodium hydride/methyl iodide when tetrahydrofuran was Used as solvent. Complete spectral data is presented, for the first time, for this unusual marine alpha-methoxylated fatty acid. (c) 2008 Elsevier Ireland Ltd. All rights reserved.
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