129029-32-9Relevant academic research and scientific papers
A short and elegant synthesis of (±)-streptopyrrolidine
Shaameri, Zurina,Ali, Sharifah Hidayah Sharif,Mohamat, Mohd Fazli,Yamin, Bohari M.,Hamzah, Ahmad Sazali
, p. 320 - 325 (2013)
A brief and efficient approach for the synthesis of (±)-5-benzyl-4- hydroxy-2-pyrrolidine () from phenylalanine racemate is described. The key step is the stereocontrolled reduction of the keto functionality of benzylated pyrrolidinone intermediate () via sodium borohydride in carboxylic acid medium furnishing both (R,R)- and (S,S)-configured diastereomers. The natural (R,R) enantiomer (), however, crystallized out from its racemic mixture. Structure of was confirmed by NMR, IR, elemental analyzer, and single crystal X-ray crystallographic techniques.
A facile approach to trans-4,5-pyrrolidine lactam and application in the synthesis of nemonapride and streptopyrrolidine
Huang, Wei,Ma, Jing-Yi,Yuan, Mu,Xu, Long-Fei,Wei, Bang-Guo
, p. 7829 - 7837 (2011/10/12)
An efficient approach to trans-4-hydroxylpyrrolidine lactams 1 starting from amino acid is described. The utility of this method has been demonstrated in the synthesis of antipsychotic nemonapride 3 and antiangiogenic streptopyrrolidine 4. Compared four s
Stereoselective synthesis of four possible isomers of streptopyrrolidine
Mohapatra, Debendra K.,Thirupathi, Barla,Das, Pragna P.,Yadav, Jhillu S.
experimental part, p. 34 - 39 (2011/03/22)
The synthesis of (4R,5R)-streptopyrrolidine (1), (4S,5R)-streptopyrrolidine (2) (4R, 5S)-streptopyrrolidine (3) and (4S,5S)-strepto- pyrrolidine (4) have been achieved in a concise and highly efficient manner via a highly stereoselective aldol type reacti
A versatile approach to cis-5-substituted 4-hydroxy-2-pyrrolidinones: asymmetric synthesis of angiogenesis inhibitor streptopyrrolidine
Xiang, Shao-Hua,Yuan, Hong-Qiu,Huang, Pei-Qiang
experimental part, p. 2021 - 2026 (2010/02/28)
A concise, flexible, and highly diastereoselective approach to cis-5-alkyl-4-hydroxy-2-pyrrolidinones 1 is described. The key step is an ammonium acetate-assisted catalytic hydrogenation of the enamides 9, derived in two steps from malimides 6a,b as we ha
Application of the asymmetric aminohydroxylation reaction for the syntheses of HIV-protease inhibitor, hydroxyethylene dipeptide isostere and γ-amino acid derivative
Kondekar, Nagendra B.,Kandula, Subba Rao V.,Kumar, Pradeep
, p. 5477 - 5479 (2007/10/03)
An enantioselective synthesis of lactone 1, a precursor to the (2R,4S,5S) hydroxyethylene dipeptide isostere and amino acid AHPPA 2 has been accomplished from the common intermediate 5 employing Sharpless asymmetric aminohydroxylation as the key step.
A novel Wittig reaction of oxazolidinones: Stereospecific synthesis of N-BOC-(3S,4S)-statine and N-BOC-(3S,4S)-AHPPA
Vidyasagar Reddy,Venkat Rao,Iyengar
, p. 775 - 776 (2007/10/03)
Stereospecific synthesis of N-BOC-(3S,4S)-Statine and N-BOC-(3S,4S)- AHPPA is achieved via a novel Wittig reaction of oxazolidinones in an efficient manner.
Tetramic Acid Chemistry. Part 1. Reinvestigation of Racemisation during the Synthesis of Tetramic Acids via Dieckmann Cyclisation
Poncet, Joel,Jouin, Patrick,Castro, Bertrand,Nicolas, Louisette,Boutar, Mohamed,Gaudemer, Alain
, p. 611 - 616 (2007/10/02)
Epimerisation during the synthesis of tetramic acids by Dieckmann cyclisation of the corresponding chiral N-acyl-α-amino esters was investigated.In the case of the isoleucine derivative, the extent of epimerisation was directly evaluated by 1H NMR analysis of the 3-acylated tetramic acids (3a,b) and (5a).A chemical correlation was carried out in the case of the 5-benzyl derivative (8h).The moderate overall yield and the partial epimerisation at position C-5 limit the usefulness of this approach for tetramic acid preparation.
