236412-69-4Relevant articles and documents
Enantioselective organocatalysis-based synthesis of 3-hydroxy fatty acids and fatty γ-lactones
Bourboula, Asimina,Limnios, Dimitris,Kokotou, Maroula G.,Mountanea, Olga G.,Kokotos, George
, (2019/06/10)
3-Hydroxy fatty acids have attracted the interest of researchers, since some of them may interact with free fatty acid receptors more effectively than their non-hydroxylated counterparts and their determination in plasma provides diagnostic information regarding mitochondrial deficiency. We present here the development of a convenient and general methodology for the asymmetric synthesis of 3-hydroxy fatty acids. The enantioselective organocatalytic synthesis of terminal epoxides, starting from long chain aldehydes, is the key-step of our methodology, followed by ring opening with vinylmagnesium bromide. Ozonolysis and subsequent oxidation leads to the target products. MacMillan’s third generation imidazolidinone organocatalyst has been employed for the epoxide formation, ensuring products in high enantiomeric purity. Furthermore, a route for the incorporation of deuterium on the carbon atom carrying the hydroxy group was developed allowing the synthesis of deuterated derivatives, which may be useful in biological studies and in mass spectrometry studies. In addition, the synthesis of fatty γ-lactones, corresponding to 4-hydroxy fatty acids, was also explored.
Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation
Pirrung, Michael C.,Zhang, Fa,Ambadi, Sudhakar,Gangadhara Rao
, p. 8367 - 8375 (2016/09/09)
Solution-phase syntheses of three bioactive natural products of mixed polypeptide-polyketide biogenesis, fellutamides A, B, and C, have been achieved. Three peptide bonds are generated without the use of coupling reagents in each synthesis of the fellutamides, which act against proteasomes.
Asymmetric routes to pentadec-1-en-4-ol: Application to the syntheses of aculeatins F and epi-F, (R)- and (S)-5-hexadecanolide and a formal synthesis of solenopsin
Harbindu, Anand,Sharma, Brijesh M.,Kumar, Pradeep
, p. 305 - 314 (2013/04/24)
A short and simple route to the synthesis of pentadec-1-en-4-ol, an important synthetic building block for the aculeatins F and epi-F, insect pheromone 5-hexadecanolide, solenopsin and various other natural products has been developed via proline-catalyze
Total synthesis of caminoside B, a novel antimicrobial glycolipid isolated from the marine sponge Caminus sphaeroconia
Zhang, Zaihong,Zong, Chengli,Song, Gaopeng,Lv, Guokai,Chun, Yuexing,Wang, Peng,Ding, Ning,Li, Yingxia
experimental part, p. 750 - 760 (2010/06/21)
The first total synthesis of caminoside B, a novel marine antimicrobial glycolipid isolated from the marine sponge Caminus sphaeroconia, was developed. This marine small molecule inhibitor (IC50 = 20 μM) targeting type III secretory pathway of
Enantioselective linchpin catalysis by SOMO catalysis: An approach to the asymmetric a-chlorination of aldehydes and terminal epoxide formation
Amatore, Muriel,Beeson, Teresa D.,Brown, Sean P.,MacMillan, David W. C.
supporting information; experimental part, p. 5121 - 5124 (2009/12/07)
Time for SOme MOre: For the first time SOMO (singly occupied molecular orbital) activation has been exploited to allow a new approach to the α-chlorination of aldehydes. This transformation can be readily implemented as part of a linchpin catalysis approach to the enantioselective production of terminal epoxides.
Studies towards lipid A: a synthetic strategy for the enantioselective preparation of 3-hydroxy fatty acids
Guaragna, Annalisa,Nisco, Mauro De,Pedatella, Silvana,Palumbo, Giovanni
, p. 2839 - 2841 (2007/10/03)
A short and efficient enantioselective synthesis of (R)-3-hydroxydodecanoic acid is described, involving a Sharpless asymmetric dihydroxylation to produce the required (R)-stereochemistry.
