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
Structure and biological activity of neopeptins A, B and C, inhibitors of fungal cell wall glycan synthesis
Ubukata,Uramoto,Uzawa,Isono
, p. 357 - 365 (2007/10/02)
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