Dimethylformamide Acetals and Bredereck’s Reagent as Building Blocks in Natural Products Total Synthesis

Author(s): Franz Bracher*

Journal Name: Mini-Reviews in Organic Chemistry

Volume 17 , Issue 1 , 2020

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Graphical Abstract:


Dimethylformamide acetals and Bredereck’s reagent (tert-butoxy-bis(dimethylamino) methane) are versatile C1 building blocks due to their ability to undergo condensation reactions with CH-acidic methyl and methylene moieties. Subsequent modulation of the resulting condensation products enables the preparation of open-chain products like aldehydes, ketones, enones, enol ethers, methyl groups, and, most important in alkaloid total synthesis, the annulation of heterocyclic rings like pyridines, pyridine-N-oxides, bromopyridines, aminopyridines, aminopyrimidines, pyrroles and chromenones. In certain cases, these reagents can act as alkylating agents. The applications of these building blocks in natural products total synthesis are reviewed here.

Keywords: Alkaloid, annulation, Bredereck's reagent, condensation, cyclization, dimethylformamide acetal, indole, naphthyridine, pyridoacridine, total synthesis.

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