Shenglin Lu

Benzannulation of Indoles to Carbazoles and Its Applications for Syntheses of Carbazole Alkaloids

A novel and efficient method for the benzannulation of indoles to carbazoles is reported. γ-Carbonyl tert-butylperoxide is applied as a new diene building block for the π-extension of simple indoles. The synthetic utility of this method is demonstrated by concise and selective total syntheses of naturally occurring carbazole alkaloids, olivacine, and asteropusazole A.

Iron-Catalyzed Acylation-Oxygenation of Terminal Alkenes for the Synthesis of Dihydrofurans Bearing a Quaternary Carbon

Iron-catalyzed acylation-oxygenation of terminal alkenes is reported. Acyl radicals generated by the oxidation of aldehydes add to terminal alkenes and followed by intramolecular oxygenation give functionalized 2,3-dihydrofuran derivatives bearing a quaternary carbon.

Hydroxysulfenylation of Electron-Deficient Alkenes through an Aerobic Copper Catalysis

A copper-catalyzed hydroxysulfenylation of α,β-unsaturated esters/amides is reported. The method presents a selective and efficient synthesis of β-hydroxysulfides bearing electron-withdrawing groups. The synthetic utility of this method is demonstrated by the concise synthesis of the anticancer drug bicalutamide.

The rearrangement of tert-butylperoxides for the construction of polysubstituted furans.

The Brønsted acid catalyzed rearrangement of tert-butyl peroxides provides a new strategy to construct 2,3-disubstituted furans via 1,2-aryl migration. In addition, tert-butyl peroxides could also be transformed into 2,3,5-trisubstituted or 2,5-disubstituted furans through a sequence of base-catalyzed Kornblum-DelaMare rearrangements and acid-promoted Paal-Knorr reactions.

Diastereoselective building up polycyclic tetrahydrofurans via tandem annulation of 1,n-enynes with aliphatic acids

A silver-catalyzed tandem annulation of aniline-linked 1,7-enynes with aliphatic acids has been reported. This synergistic tandem annulations allow the straightforward and efficient building up various highly diastereoselective polycyclic tetrahydrofurans. Primary and secondary acids undergo decarboxylation/cascade radical addition/α-C(sp3)–H cleavage/cycloalkylation/O-trapping to generate oxygenous [6.6.6.5] fused products. While tertiary acids undergo decarboxylation/cascade radcial addition/β-C(sp3)–H cleavage/O-trapping to give oxygenous [6.6.6.6] fused products.