A series of electron withdrawing or donating group substituted phenols were chemoselectively arylated with various substituted bromo-nitroarenes using KO(t)Bu at room temperature via an SNAr pathway. The synthesis of natural alkaloids (carbazoles), dibenzofurans, and a biaryl-indole was achieved from the synthesized nitro-biaryl-ols.

Three monoterpenoid gluco-indole alkaloids, 3beta-isodihydrocadambine, cadambine, and 3alpha-dihydrocadambine, were isolated from Nauclea cadamba ROXB. growing in Thailand. The stereochemistry at C19 in 3beta-isodihydrocadambine was elucidated to be R by spectroscopic analysis. Treatment of 3alpha-dihydrocadambine with beta-glucosidase in aqueous ammonium acetate solution gave an indolopyridine...

The first total synthesis of malagashanine, a chloroquine potentiating indole alkaloid, is presented. A highly stereoselective cascade annulation reaction was developed to generate the tetracyclic core of the Malagasy alkaloids. This chemistry is likely to be broadly applicable to the synthesis of other members of this stereochemically unique family of natural products.

The syntheses and biosyntheses of the paraherquamide and brevianamide families of prenylated indole-derived alkaloids are reviewed. It has been proposed that the unique bicyclo[2.2.2]diazaoctan ring system that is common to this family of natural products, arises by a biological intramolecular Diels-Alder cycloaddition reaction. Both synthetic approaches and total syntheses of several members o...

Rational engineering of complicated metabolic networks involved in the production of biologically active plant compounds has been greatly impeded by our poor understanding of the regulatory and metabolic pathways underlying the biosynthesis of these compounds. Whereas comprehensive genome-wide functional genomics approaches can be successfully applied to analyze a select number of model plants,...

Ervatamia coronaria (Apocynaceae) is a glabrous, evergreen tree commonly grown in the gardens of West Pakistan. Various parts of the plant are used in the indigenous system of medicine for the treatment of ophthalmia, for application on wounds and inflammed parts of the body, as anthelmintic etc. A number of indole alkaloids have previously been reported from the leaves, stem bark and roots of ...