Synthesis of C(3) benzofuran-derived bisaryl quaternary centers: approaches to diazonamide A.

Synthesis of heterocyclic natural products: Model studies towards diazonamide A

Model studies towards the total synthesis of the cytotoxic marine natural product diazonamide A are described. The approach uses rhodium(I1) catalysed reactions of diazocarbonyl compounds in 4 key steps; the construction of the oxazole rings by the rhodium(I1) catalysed addition of diazocarbonyl compounds to nitriles, and of the indole and benzofuran tinits by rhodium(l1) mediated intramolecula...

Total synthesis of diazonamide A.

A total synthesis of the marine natural product diazonamide A (1) has been accomplished. This work features a highly stereoselective synthesis of the C(10) quaternary center and the central furanoindoline core enabled by an iminium-catalyzed alkylation-cyclization cascade. Additionally, a magnesium-mediated intramolecular macroaldolization and a palladium-catalyzed tandem borylation/annulation ...

Approaches to the quaternary stereocentre and to the heterocyclic core in diazonamide A using the Heck reaction and related coupling reactions.

In model studies towards the quaternary centre at the heart of diazonamide A (early structure 2; revised structure 1), cyclisations of the alkene-substituted iodoaryls 4, 13, 18 and 23, under Heck reaction conditions, were shown to lead to the corresponding benzodihydrofuran 5, benzofuranone 14 and the oxindoles 19 and 24 respectively, in 50-80% yield. Further manipulation of the benzodihydrofu...

A concise formal synthesis of diazonamide A by the stereoselective construction of the C10 quaternary center.

Chemistry and biology of diazonamide A: second total synthesis and biological investigations.

As an especially unique target for chemical synthesis, diazonamide A has the potential to be constructed through a plethora of synthetic routes, each attended by different challenges and opportunities for discovery. In this article, we detail our second total synthesis of diazonamide A through a sequence entirely distinct from that employed in our first campaign, one whose success required the ...