4669-02-7Relevant articles and documents
Synthesis and evaluation of analogues of the glycinocin family of calcium-dependent antibiotics
Corcilius, Leo,Liu, Dennis Y.,Ochoa, Jessica L.,Linington, Roger G.,Payne, Richard J.
, p. 5310 - 5320 (2018/08/03)
The glycinocins are a class of calcium-dependent, acidic cyclolipopeptide antibiotics that are structurally related to the clinically approved antibiotic daptomycin. In this article, we describe the synthesis of a small library of glycinocin analogues that differ by variation in the exocyclic fatty acyl substituent. The glycinocin analogues were screened against a panel of Gram-positive bacteria (as well as Gram-negative P. aeruginosa). These analogues exhibited similar calcium-dependent activity to the parent natural products against Gram-positive bacteria but showed no activity against P. aeruginosa. The length of the fatty acid was shown to be important for optimal biological activity, while the hybridisation at the α,β position and branching within the fatty acyl chain had only subtle effects on activity.
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.
METHOD FOR PRODUCING CROSS-COUPLING COMPOUND
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Page/Page column 13-14, (2010/01/29)
To provide a method for performing a cross-coupling reaction of a Grignard compound with an alkyl halide simply, efficiently and in high yield, a method for obtaining a ω-bromo long chain carboxylic acid simply and efficiently using an easily obtainable raw material and a method for producing a useful branched fatty acid simply and efficiently. [R1: an alkyl group having 1 to 15 carbon atoms, R2: an alkyl group having 1 to 30 carbon atoms with a carboxyl group and X and X': a halogen atom] [n : an integer of 9 to 17] [n : an integer of 9 to 17, R1a : a branched alkyl group having 3 to 8 carbon atoms and X: a halogen atom]