Synthesis and Absolute Configuration of Novel N,O-Psiconucleosides Using (R)-N-Phenylpantolactam as a Resolution Agent

Abstract

A series of novel N,O-psiconucleosides has been prepared in both enantiomeric forms by resolution of an advanced racemic synthetic intermediate using (R)-N-phenylpantolactam as a chiral resolution agent. The absolute configuration of all of these compounds has been unequivocally established by chemical correlation with the novel (R)- or (S)-1-methyl-5-phenylpyrrolidine-2,3-dione, prepared from the known (R)- and (S)-1-methyl-5-phenylpyrrolidin-2-one, respectively.

Truncated phosphonated C-1′-branched N,O-nucleosides: A new class of antiviral agents

“…5,[12][13][14][15] More recently, the use of a chiral auxiliary has promoted the enantioselective synthesis of a series of psiconucleosides. 16 However, none of the reported compounds has shown a remarkable biological activity, probably due to the lack of efficient phosphorylation towards the triphosphate derivatives, the active form of nucleoside RT inhibitors.…”

Asymmetric synthesis of γ-aryl-substituted GABA derivatives via a highly diastereoselective Rh-catalyzed boronic acid addition at room temperature

“…The absolute configuration of the product (2a) was confirmed by the rotation of the lactamized product [(−)-(S)-5-phenylpyrrolidin-2-one] reported in the literature. 23 On the basis of analogy with 2a, we believe that we have obtained the (4S)-isomer for all of the GABA derivatives 2b-g described subsequently.…”

Highly stereoselective double (R)-phenylglycinol-induced cyclocondensation reactions of symmetric aryl bis(oxoacids)

“…The combined organic extracts were washed with saturated NaHCO 3 solution, brine, and water, dried and concentrated. Flash chromatography (1 : 1 hexane-EtOAc) afforded 14 (530 mg, 70%) as a yellow oil: IR (film) 1693, 2800-3000 cm -1 ; 1 H NMR (CDCl (S)-5-Phenyl-2-pyrrolidone (15) 17 5 M aqueous H 2 SO 4 (15 mL) was added to a solution of 14 (400 mg, 1.5 mmol) in Et 2 O (60 mL). Then, the resulting mixture was stirred at reflux temperature until no more starting material was observed by TLC (20 h).…”

“…3 , 400 MHz) d 1.98 (m, 1H, H-4), 2.36-2.50 (m, 2H, H-4 and H-3), 2.56 (m, 1H, H-3), 4.75 (t, J = 7.1 Hz, 1H, H-5), 6.23 (br s, 1H, NH), 7.27-7.33 (m, 3H, ArH), 7.34-7.40 (m, 2H, ArH); 13 C NMR (CDCl 3 , 100.6 MHz) d 30.3 (CH 2 , C-4), 31.2 (CH 2 , C-3), 58.1 (CH, C-5), 125.6 (2 CH, Ph), 127.8 (CH, Ph), 128.8 (2 CH, Ph), 128.8 (CH, Ph), 142.5 (C, Ph), 178.6 (C, CON); [a] 22 D -58.7 (c 1.0, CHCl 3 ) {lit 17. …”