Although isothiocyanate and indole compounds derived from cruciferous vegetables appear to be structurally unrelated, they are both derived from glucosinolates. These sulfur-containing glycosides are found in the order Capparales, which includes the large family Brassicaceae. The glucosinolate molecule comprises a common glucone moiety and a variable aglucone side-chain, derived from one of sev...

This article reviews the mechanisms by which glucosinolate breakdown products are thought to inhibit carcinogenesis. It describes how isothiocyanates, thiocyanates, nitriles, cyano-epithioalkanes and indoles are produced from glucosinolates through the actions of myrosinase, epithiospecifier protein and epithiospecifier modifier protein released from cruciferous vegetables during injury to the ...

Unprecedented synthesis of functionalized indoles of potential pharmacological interest has been developed via a Pd-mediated cascade reaction involving an intramolecular Heck coupling followed by the construction of a fused cyclopentane ring in a single pot.

An efficient methodology for the synthesis of a series of new fused polyclyclic indoles has been developed by Brønsted acid-catalyzed intramolecular Friedel-Crafts reactions of properly designed indolyl alcohols.

The first palladium-catalyzed dearomative cyclization via a modified Catellani-type C-H functionalization has been realized. The new strategy led to a series of spiroindolenine derivatives bearing an all-carbon quaternary spirocenter from simple aryl halides and substituted indoles.

A copper-catalyzed method for the preparation of ynamides has been identified that proceeds via aerobic oxidative coupling of terminal alkynes with various nitrogen nucleophiles, including cyclic carbamates, amides and ureas, and N-alkyl-arylsulfonamides and indoles.

A series of 2-substituted 3-(toluenesulfonamidoalkyl)indoles was synthesized by application of (EtO)(2)POH or iodine as the catalyst, and was hydrogenated using chiral Pd catalyst, giving the 2,3-disubstituted indolines with up to 97% ee.

The application of a novel solid-phase synthesis of 2,3-disubstituted indoles utilizing a carbamate indole linker is described resulting in the identification of the novel, high-affinity, selective h5-HT2A antagonist 19.

Tandem palladium-catalysed aryl and alkenyl C-N bond formation allows the synthesis of a variety of indoles bearing sterically demanding N-substituents, including the natural product demethylasterriquinone A1.