1931-63-1Relevant articles and documents
N-(17-Acyloxy-acyl)-glutamines: Novel Surfactants from Oral Secretions of Lepidopteran Larvae
Spiteller, Dieter,Boland, Wilhelm
, p. 8743 - 8749 (2003)
N-(17-Acyloxy-acyl)-glutamine conjugates such as N-(17-linolenoyloxy-linolenoyl)-glutamine (6), N-(17-linolenoyloxy-linoleoyl)-glutamine (7), N-(17-linoleoyloxy-linolenoyl)-glutamine (8), and N-(17-linoleoyloxy-linoleoyl)-glutamine (9) were identified as novel surfactants in the oral secretion of several lepidopteran larvae (S. exigua, S. littoralis, S. frugiperda, and H. virescens) by LC-MS/MS and chemical degradation. Authentic reference compounds were synthesized via a dissymmetric bis-Wittig approach and confirmed the assigned structures.
Stereocontrolled synthesis of the PPAR-γ agonist 10-nitrolinoleic acid
Dunny, Elizabeth,Evans, Paul
, p. 5334 - 5336 (2010)
(Figure presented) The naturally occurring PPAR-γ ligand 10-nitrooctadeca-9(E),12(Z)-dienoic acid (10-nitrolinoleic acid) (2a) was prepared as a single regio- and geometrical isomer in a practical eight-step, convergent sequence. The synthetic route featured a nitro aldol reaction between 9-oxononanoic acid methyl ester (3) and 1-nitronon-3(Z)-ene (4) in the key carbon-carbon bond forming step. The ability of 2a (and its methyl ester 9) to bind to PPAR-γ in a ligand-binding assay is reported.
Bergmann
, p. 2279 (1941)
Total Synthesis of α-Ketol Derivative of Linolenic Acid (KODA), a Flower-inducing Factor in Lemna paucicostata
Yokokawa, Yoshihiro,Kobayashi, Kouji,Yokoyama, Mineyuki,Yamamura, Shosuke
, p. 844 - 845 (2003)
Racemic 9-hydroxy-10-oxo-12(Z), 15(Z)-octadecadienoic acid [(±)-KODA] was synthesized via a coupling reaction between a diyne and an epoxide derived from methyl oleate as a key step. An optically active 9R-KODA was also synthesized by enantioselective lipase-catalyzed esterification of an allyl alcohol. Both synthetic (±)-KODA and 9K-KODA showed remarkable flower-inducing activity in Pharbitis nil.
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Gerlach,H. et al.
, p. 1226 - 1231 (1978)
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Biobased Aldehydes from Fatty Epoxides through Thermal Cleavage of β-Hydroxy Hydroperoxides**
De Dios Miguel, Thomas,Duc Vu, Nam,Lemaire, Marc,Duguet, Nicolas
, p. 379 - 386 (2020/11/30)
The ring-opening of epoxidized methyl oleate by aqueous H2O2 has been studied using tungsten and molybdenum catalysts to form the corresponding fatty β-hydroxy hydroperoxides. It was found that tungstic acid and phosphotungstic acid gave the highest selectivities (92–93 %) towards the formation of the desired products, thus limiting the formation of the corresponding fatty 1,2-diols. The optimized conditions were applied to a range of fatty epoxides to give the corresponding fatty β-hydroxy hydroperoxides with 30–80 % isolated yields (8 examples). These species were fully characterized by 1H and 13C NMR spectroscopy and HPLC-HRMS, and their stability was studied by differential scanning calorimetry. The thermal cleavage of the β-hydroxy hydroperoxide derived from methyl oleate was studied both in batch and flow conditions. It was found that the thermal cleavage in flow conditions gave the highest selectivity towards the formation of aldehydes with limited amounts of byproducts. The aldehydes were both formed with 68 % GC yield, and nonanal and methyl 9-oxononanoate were isolated with 57 and 55 % yield, respectively. Advantageously, the overall process does not require large excess of H2O2 and only generates water as a byproduct.
Synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide
Eskandari, Roozbeh,Hess, Jeremy P.,Tochtrop, Gregory P.
supporting information, p. 7136 - 7139 (2021/07/28)
Herein, a new protocol for rapid synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide is described. This approach comprises two sequential chemoselective reactions between sulfonium and phosphonium ylides and two distinct aldehydes, which allows for the rapid construction of a variety of unsymmetric α,β-unsaturated epoxy ketones. This methodology allows the rapid construction of the core reactive functionality of a family of lipid peroxidation products, the epoxyketooctadecenoic acids, but can be further broadly utilized as a useful synthon for the synthesis of natural products, particularly those derived from oxidized fatty acids. Accordingly, a protocol utilizing this approach to synthesize the epoxyketooctadecenoic acid family of molecules is described.
