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

Author(s):

Franz Bracher*   Pages 1 - 20 ( 20 )

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:

Dimethylformamide acetal, Bredereck`s reagent, condensation, alkaloid, cyclization, annulation, indole, pyridoacridine, naphthyridine, total synthesis

Affiliation:

Department of Pharmacy – Center for Drug Research, Ludwig-Maximilians University, Munich



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