2724-57-4Relevant articles and documents
A practical synthesis of long-chain iso-fatty acids (iso-C 12-C19) and related natural products
Richardson, Mark B.,Williams, Spencer J.
, p. 1807 - 1812 (2013/10/22)
A gram-scale synthesis of terminally-branched iso-fatty acids (iso-C 12-C19) was developed commencing with methyl undec-10-enoate (methyl undecylenate) (for iso-C12-C14) or the C15 and C16 lactones pentadecanolide (for iso-C 15-C17) and hexadecanolide (for iso-C18-C 19). Central to the approaches outlined is the two-step construction of the terminal isopropyl group through addition of methylmagnesium bromide to the ester/lactones and selective reduction of the resulting tertiary alcohols. Thus, the C12, C17 and C18 iso-fatty acids were obtained in three steps from commercially-available starting materials, and the remaining C13-C16 and C19 iso-fatty acids were prepared by homologation or recursive dehomologations of these fatty acids or through intercepting appropriate intermediates. Highlighting the synthetic potential of the iso-fatty acids and various intermediates prepared herein, we describe the synthesis of the natural products (S)-2,15-dimethylpalmitic acid, (S)-2-hydroxy-15-methylpalmitic acid, and 2-oxo-14-methylpentadecane.
Synthesis and Absolute Configuration of 2-Hydroxy-12-methyl Tridecanoic Acid
Balzer, Th.,Budzikiewicz, H.
, p. 1367 - 1368 (2007/10/02)
The synthesis of racemic 2-hydroxy-12-methyl tridecanoic acid is described.The absolute configuration of the two enantiomers has been determined by the method of Dale and Mosher. - Keywords: 2-Hydroxy-12-methyl Tridecanoic Acid, Absolute COnfiguration
Biosynthetic Studies of Marine Lipids. 5. The Biosynthesis of Long-Chain Branched Fatty Acids in Marine Sponges
Carballeira, Nestor,Thompson, Janice E.,Ayanoglu, Eser,Djerassi, Carl
, p. 2751 - 2756 (2007/10/02)
The very long chain branched fatty acids 25-methyl-5,9-hexacosadienoic (Δ5,9-iso-27:2)-and 24-methyl-5,9-hexacosadienoic (Δ5,9-anteiso-27:2) acids as well as the straight-chain 5,9-hexacosadienoic (Δ5,9-26:2) acid were shown to originate from the short-chain precursors 13-methyltetradecanoic (iso-15:0), 12-methyltetradecanoic (anteiso-15:0), and palmitic (n-16:0) acids, respectively, by means of 14C incorporation experiments in the marine sponge Jaspis stellifera.These results confirm that methyl branching does not occur after chain elongation.The unusual Δ5,9 unsaturation probably takes place after chain elongation of short branched or straight-chain fatty acids.