Total Syntheses of the 3-Pyrrolo[2,3-]quinolone-Containing Alkaloids Marinoquinolines A-F, K, and Aplidiopsamine A Using a Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Pathway.

Compounds - and representing key members of the marinoquinoline family of natural products, together with the related marine alkaloid aplidiopsamine A (), have been synthesized using various combinations of palladium-catalyzed Ullmann cross-coupling and reductive cyclization processes involving a C3-arylated pyrrole as the common intermediate. These natural products have been characterized by single-crystal X-ray analyses and evaluated as inhibitors of acetylcholinesterase (AChE) with congener proving to be the most active.

Modular total syntheses of the marine-derived resorcylic Acid lactones cochliomycins a and B using a late-stage nozaki-hiyama-kishi macrocyclization reaction.

The natural products cochliomycin A (1) and cochliomycin B (2), two resorcylic acid lactones obtained from marine sources, have been prepared in a concise and stereocontrolled manner from the readily accessible building blocks 4-6. Olefin cross-metathesis, trans-esterification and Nozaki-Hiyama-Kishi (NHK) macrocyclization reactions were employed in the key steps. Hydrolysis of the immediate precursor to cochliomycin B affords the resorcylic acid lactone zeaenol (24).

A tandem catalytic approach to methyleneindenes: mechanistic insights into gem-dibromoolefin reactivity.

The methylenindene scaffold can be prepared from readily available gem-dibromoolefins using an efficient palladium-catalyzed tandem intermolecular Suzuki/intramolecular Heck reaction. The reaction is highly modular and proceeds under mild conditions. The choice of ligand was found to be crucial to control the selectivity of the reaction.

Intramolecular cross-coupling of gem-dibromoolefins: a mild approach to 2-bromo benzofused heterocycles.

Highly useful halogenated benzofurans and benzothiophenes are prepared from readily available gem-dibromoolefins using a mild, ligand-free copper catalyzed cross-coupling procedure.

Silver-promoted domino Pd-catalyzed amination/direct arylation: access to polycyclic heteroaromatics.

Novel tetracyclic and pentacyclic indole derivatives can be prepared from readily available gem-dibromovinyl substrates in a single step by means of an efficient Pd-catalyzed domino Buchwald-Hartwig amination/direct arylation reaction. Enhanced reactivity and selectivity are obtained by the addition of silver salts.