Nucleotide competing reverse transcriptase inhibitors: Discovery of a series of non-basic benzofurano[3,2-d]pyrimidin-2-one derived inhibitors

Catalytic Enantioselective Intramolecular Oxa-Michael Reaction to α,β-Unsaturated Esters and Amides

“…4d was directly converted to alcohol 5j 25 in 98% yield using SmI 2 and Et 3 N, providing access to lipoic acid (7) 26 precursor 6 27 and NcRTI inhibitor 8. 28 Isochroman product 4aq could also be reduced according to literature precedent to corresponding alcohol 5k, 29 a key intermediate in the synthesis of highly selective D 4 receptor antagonist Sonepiprazole (9). 5d To elucidate the origin of stereocontrol in the BIMPcatalyzed intramolecular oxa-Michael reaction to α,β-unsaturated esters, density functional theory (DFT) calculations at COSMO(THF)-ZORA-M06-2X/TZ2P//COSMO(THF)-ZORA-BLYP-D3(BJ)/DZP were performed using Amsterdam Density Functional (ADF) software package (Figure 1).…”

“…Next, selected oxa-Michael products were converted into valuable drug and natural product intermediates (Scheme C). 4d was directly converted to alcohol 5j in 98% yield using SmI 2 and Et 3 N, providing access to lipoic acid ( 7 ) precursor 6 and NcRTI inhibitor 8 . Isochroman product 4aq could also be reduced according to literature precedent to corresponding alcohol 5k , a key intermediate in the synthesis of highly selective D 4 receptor antagonist Sonepiprazole ( 9 )…”

2-(Tetrahydrofuran-2-yl)acetic Acid and Ester Derivatives as Long-Range Pollinator Attractants in the Sexually Deceptive Orchid Cryptostylis ovata

“…The absolute configuration of the natural products was confirmed by preparing ( R )- 1 and ( S )- 1 from tetrahydrofuran-2-carboxylic acid − of known configuration, purchased from Enamine Ltd., Ukraine. The specific rotations of the R - and S -enantiomers of tetrahydrofuran-2-carboxylic acid, respectively were confirmed beforehand: [α] 22 D +16.0 and −15.6 (CHCl 3 ) respectively.…”

Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones

“…It is likely that the harsh thermal conditions required for the coupling are not tolerated with the highly electrophilic ketimine moiety of 4-trifluoromethylpyrimidin-2(1 H )-ones. The CEL reaction was successfully applied in the N -arylation of many heterocyclic systems [ 35 – 37 ] including non-fluorinated pyrimidin-2(1 H )-ones [ 38 – 39 ] under mild conditions. There are a few thorough studies on this reaction with pyrimidine and purine nucleoside bases and their derivatives which are most closely related to fluorine-containing substrates 1 [ 40 – 42 ].…”