Asymmetric Syntheses of Oxindole and Indole Spirocyclic Alkaloid Natural Products

Abstract

This review highlights the advances in the literature up to May 2009 in the synthesis of spirocyclic indoline natural products. The focus is on formation of the spirocyclic chiral center, including both enantioselective and diastereoselective methods. This review is split into two main sections, the first consisting of the formation of spirooxindoles and their application towards oxindole alkaloids, and the second covering asymmetric synthesis of spiroindoline natural products. Conclusion

Crystal structure of 3-hydroxy-3-phenyl-1,3-dihydro-2H-indol-2-one, C14H11NO2

“…3-Substituted 3-hydroxyoxindoles are attractive compounds in organic synthesis because they are frequently found in many alkaloids, some natural substances and in pharmaceutically and biologically active compounds [5][6][7]. The bond lengths and angles derived from the title structure are within normal ranges.…”

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).…”

tert-Butyl (2S,3R,4R)-7′-bromo-4-methyl-2′,5-dioxo-4,5-dihydro-3H-spiro[furan-2,3′-indoline]-3-carboxylate

“…The key structural characteristic of these compounds is the spiro ring fused at the 3-position of the oxindole core (Cerisoli et al, 2016) with varying degrees of substitution around it (Trost & Brennan, 2009;Wang et al, 2013;Monari et al, 2015). However, it is a challenge to synthesize chiral spirocyclic oxindoles with spiro quaternary centers and multiple chiral centers.…”