•3-CF3-oxindoles were obtained in good yield.•Asymmetric sulfenylation of 3-CF3-oxindole was obtained in 84% yield and with 94% ee.•The electro-donating groups of 3-CF3-oxindoles were well tolerated.•The electro-donating groups of sulfenylation reagents were well tolerated.•The electro-withdrawing groups of sulfenylation reagents were also well tolerated.An asymmetric sulfenylation of 3-CF3-oxindoles catalyzed by a quinidine derivative was described. 3-CF3-oxindoles with electro-donating groups led to corresponding products in good yield and with good enantioselectivity while 3-CF3-oxindoles bearing electro-withdrawing groups were not competent substrates due to its significant decomposition at the optimal reaction conditions. As for the sulfenylation reagents based on thiophenol, both electro-donating groups and electro-withdrawing groups were well tolerated.Download high-res image (101KB)Download full-size image

Divergent C–H functionalization reactions (arylation, carboxylation, olefination, thiolation, acetoxylation, halogenation, naphthylation) using a pyridazinone moiety as an internal directing group were successfully established. This approach offers a late-stage, ortho-selective diversification of a biologically active pyridazinone scaffold. Seven series of novel pyridazinone analogues were synthesized conveniently as the synthetic precursors of potential sortase A (SrtA) inhibitors.

Amino acid esters of nucleosides at 5′-position, as peptidomimetic prodrugs, which could be actively transported by the intestinal oligopeptide transporters 1 (PepT1), bear improved oral bioavailability. We established here a regioselective synthesis of the 5′-esters of some nucleosides via an orthogonal protecting protocol with triphenylmethyl (Tr) and allyloxycarbonyl (AOC) protecting groups. A series of 5′-esters of cytarabine and gemcitabine were selectively synthesized in over 36.0% total yields. This efficient and robust methodology will be examplified for the further study of the prodrugs of large number of antiviral and anticancer nucleosides.

The first total synthesis of viequeamide A, a natural cyclic depsipeptide isolated from a marine button cyanobacterium, was achieved with the N-Me-Val–Thr peptide bond as the final macrocyclization site. The synthetic product gave nearly identical spectroscopic data to that reported for the natural product.

Divergent C–H functionalization reactions (arylation, carboxylation, olefination, thiolation, acetoxylation, halogenation, naphthylation) using a pyridazinone moiety as an internal directing group were successfully established. This approach offers a late-stage, ortho-selective diversification of a biologically active pyridazinone scaffold. Seven series of novel pyridazinone analogues were synthesized conveniently as the synthetic precursors of potential sortase A (SrtA) inhibitors.