Construction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids

Abstract

The spiro[pyrrolidine‐3,3′‐oxindole] ring system is found at the core of a number of alkaloids, which possess significant biological activity and are interesting, challenging targets for chemical synthesis. In the present review, we report on the different strategies for the synthesis of the spiro[pyrrolidine‐3,3′‐oxindole] ring system in the context of recent synthesis of coerulescine, horsfiline, elacomine, salacin, pteropodine, alstonisine, spirotryprostatin A and B, and strychnofoline. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

Palladium(0)-Catalyzed Benzylic C(<i>sp</i>³)–H Functionalization for the Concise Synthesis of Heterocycles and Its Applications

“…Spirooxindole natural products, which are characterized by the fused spiro-structure of their oxindole core bearing various rings at its C3 position, have attracted considerable attention from numerous synthetic chemistry groups because of their complex structures and their pronounced biological activities [44][45][46][47][48][49][50][51][52][53] (Fig. 1).…”

“…Because the carbamoyl moiety was fixed by the rigid tricyclic skeleton, the C-H bond of the methyl group was positioned further away from the Pd center compared with the simple carbamoyl chlo- (51). In contrast, the oxidation of 62a with BaMnO 4 gave pratosine (52).…”

An efficient synthesis of bis-indolyloxindoles from (phenylimino)indolin-2-ones and 1H-indole catalyzed by Citric acid

“…The scope of this reaction is exemplified with a disubstituted compound, 5,7-dimethyl-3-(phenylimino)indolin-2-one (1c) with 2 to produce the desired product (3c) in 81% yield (Table 1, entry 3). Thus, 1H-indole was used as a representative starting material and the reactions were performed with various substituted (phenylimino)indolin-2-ones such as 5-methoxy, 5-fluoro, 5-chloro, 5-bromo, 6-bromo, 5-nitro derivatives to obtain the corresponding products in good yields (Table 1, entries [4][5][6][7][8][9]. In all cases, the reactions proceeded smoothly to furnish the desired product in good to excellent yields.This method was further extended to N-methyl, N-Benzyl, N-Acetyl (phenylimino) indolin-2-ones to produce the desired products (Table 1, entries 10-12) in good yields.…”

“…The oxindole structure is featured widely in a variety of pharmacologically and biologically active compounds [1][2][3][4][5][6][7][8]. Especially, 3, 3-diaryloxindoles are known to possess mechanism-specific antibacterial, antiprotozoal, antiproliferative, and antiinflammatory activities [9].…”

[Hmim][HSO4]: An Efficient and Reusable Catalyst for the Synthesis of Spiro[dibenzo[a,i]-xanthene-14,3'-indoline]-2',8,13-triones and Spironaphthopyran[2,3-d]pyrimidine-5,3'-indolines

“…4,5 Therefore, a number of methods have been reported for the preparation of spirooxindole fused heterocycles. [6][7][8][9][10] The quinone moiety is involved in a wide variety of biochemical processes including electron transport and oxidative phosphorylation. 11 Various biological properties including enzyme inhibition, antibacterial, antifungal, and anticancer activities have been reported for quinones.…”