Starting from (S)-tryptophanol, a formal synthesis of ent-rhynchophylline and ent-isorhynchophylline, involving stereoselective cyclocondensation, spirocyclization, and alkylation reactions, and the final adjustment of the oxidation level at the oxindole and piperidine moieties, is reported.

Cycloaddition reactions between pyridinium ylides and 3-alkenyl oxindoles that proceed in high yield and with very good regio- and diastereoselectivity are reported. The resulting cycloadducts have the same stereochemistry of biologically active oxindole alkaloids, such as strychnofoline.

the ionic liquid, n,n,n,n-tetramethylguanidiniumtriflate (tmgtf) was found to be an efficient catalyst solvent for henry reaction between nitromethane and isatin derivatives to provide 3-hydroxy-3-(nitromethyl)indolin-2-one under mild conditions. the ionic liquid amenable to successive recycling without appreciable decrease in activity. synthesized compounds have been screened for their anti-di...

Quinidine derivative (QD)(2)PYR was found to catalyze the asymmetric direct amination of unprotected prochiral 3-oxindole with DIAD to construct quaternary stereocenters at the C3 position with excellent enantioselectivity.

ammonium monovanadate (nh4vo3) has been devoted as an efficient, commercially available, eco-friendly and reusable catalyst for the synthesis of bis(indolyl)methanes (bims), oxindole derivatives and also michael adducts of indoles at 50 °c under solvent-free conditions. the reusability of this solid acid catalyst in addition with its selectivity has also been examined.

Ammonium monovanadate (NH4VO3) has been devoted as an efficient, commercially available, eco-friendly and reusable catalyst for the synthesis of bis(indolyl)methanes (BIMs), oxindole derivatives and also Michael adducts of indoles at 50 °C under solvent-free conditions. The reusability of this solid acid catalyst in addition with its selectivity has also been examined.

In the title compound, C26H20N4O2S, the central pyrrolidine ring adopts a twist conformation on the C-C bond involving the spiro C atom. Its mean plane makes dihedral angles of 78.83 (14), 65.91 (15) and 44.49 (18)° with the mean planes of the adjacent oxindole ring system, the indole system and the thio-phene ring, respectively. The indole and indoline units are essentially planar, with maximu...

Expedient synthetic approaches to the highly functionalized polycyclic alkaloids communesin F and perophoramidine are described using a unified approach featuring a key decarboxylative allylic alkylation to access a crucial and highly congested 3,3-disubstituted oxindole. Described are two distinct, stereoselective alkylations that produce structures in divergent diastereomeric series possessin...

Oxindoles and their indoline derivatives are common structural motifs found in a wide array of natural and biologically active molecules. Most catalytic methods for the asymmetric syntheses of these compounds rely heavily on the use of transition-metal catalysts. In contrast, alternative catalytic procedures involving organocatalysis are scarce. Herein we disclose a conceptually novel organocat...

In the title compound, C(24)H(21)ClN(4)O(2)S, the two adjacent spiro junctions link an almost planar (r.m.s. deviation = 0.017 Å) 2-oxindole ring, a hexa-hydro-1H-pyrrolizine ring and a tetra-hydro-imidazo[2,1-b]thia-zole ring. In the crystal, inversion dimers linked by pairs of N-H⋯N hydrogen bonds occur, generating an R(2) (2)(16) loop.