128990-14-7Relevant academic research and scientific papers
Enantioselective synthesis of fatty acid amide hydrolase inhibitors with 1, 3-disubstituted butan-2-one scaffold
Sundermann, Tom R.,Lehr, Matthias
, p. 447 - 453 (2017)
Fatty acid amide hydrolase is a key enzyme in the inactivation of the analgesic and anti-inflammatory endocannabinoid anandamide. Previously, the chiral compound 1-(1H-benzotriazol-1-yl)-3-(4-phenylphenoxy)butan-2-one was identified as a potent inhibitor of fatty acid amide hydrolase and is therefore of interest as a potential agent against pain and inflammation. Two different approaches for the enantioselective synthesis of fatty acid amide hydrolase inhibitors with a 1, 3-disubstituted butan-2-one scaffold were carried out. The first one uses the chiral epoxide 2-[1-(4-phenylphenoxy)ethyl]oxirane with an (R)- or (S)-configuration at the exocyclic stereocenter as central intermediates. These substances were obtained by separation of the non-stereoselectively synthesized epoxide into its racemic diastereomers by reversed phase chromatography followed by Jacobsen's hydrolytic kinetic resolution of each enantiomer with the (S)-configured oxirane ring. Furthermore, a chiral pool based enantioselective synthesis was developed. In that case, the starting compound for both target enantiomers was methyl 3, 4-O-isopropylidene-L-threonate. In comparison to the first approach, the chiral pool synthesis consisted of more steps, but generated the enantiomers with much better enantiomeric excess. Biological evaluation showed that the (R)-enantiomer inhibits isolated fatty acid amide hydrolase with a 200-fold higher activity than the (S)-enantiomer.
Ti(iii)-mediated radical cyclization of epoxy-β-aminoacrylate in the synthesis of the substituted pyrrolidine core of necine bases: Synthesis of 2-epi-rosmarinecine
Basu, Sandip,Kandiyal, Pancham S.,Ampapathi, Ravi Sankar,Chakraborty, Tushar Kanti
, p. 13630 - 13634 (2013/08/23)
A radical-mediated approach to the necine base 2-epi-rosmarinecine is described. The synthesis is based on the stereoselective formation of a highly substituted pyrrolidine ring from β-aminoacrylate, diastereoselective allylation and intramolecular cycliz
First stereoselective total synthesis of panaxjapyne C
Thakur, Pallavi,Kumaraswamy,Raji Reddy,Bandichhor, Rakeshwar,Mukkanti
scheme or table, p. 3703 - 3705 (2012/09/21)
The first stereoselective total synthesis of polyacetylene panaxjapyne C is described. The key reactions include regioselective opening of the epoxide and Cadiot-Chodkiewicz cross-coupling reactions. l-Ascorbic acid was used as a chiral pool material for the construction of the both terminal acetylenes.
Stereoselective total synthesis of microcarpalide
Sharma,Cherukupalli, Govardhan R.
, p. 1081 - 1088 (2007/10/03)
A stereoselective total synthesis of microcarpalide using ring-closing metathesis (RCM) as a key step is reported. l-Ascorbic acid was used as a chiral pool material for the construction of the olefinic alcohol and an asymmetric aldol reaction provided the chiral precursor for the synthesis of olefinic acid.
A short, simple and general approach for the synthesis of (3S,4S)-3-methoxy-4-methylamino pyrrolidine and (3S,4R)-3-methoxy-4-methylamino pyrrolidine
Kumar, A. Ravi,Reddy, J. Santhosh,Rao, B. Venkateswara
, p. 5687 - 5689 (2007/10/03)
A general and efficient stereoselective approach for the synthesis of (3S,4S) and (3S,4R)-3-methoxy-4-methylamino pyrrolidines, a part of the structure of AG-7352, a naphthyridine antitumor agent and quinoline antibacterial compounds has been described.
Synthesis of 2-deoxy-L- and -D-galacto-heptose via inverse type hetero-Diels-Alder reaction
De Gaudenzi, Luigi,Apparao, Satyam,Schmidt, Richard R.
, p. 277 - 290 (2007/10/02)
Inverse type hetero-Diels- Alder reaction based diastereoselective synthesis of higher sugars is performed with chiral carbon substituents in the 2-position of the 1-oxa-13-diene required as heterodiene. This is demonstrated for the synthesis of partially
