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

(E-pub Ahead of Print)

Author(s): Franz Bracher* .

Journal Name: Mini-Reviews in Organic Chemistry

Become EABM
Become Reviewer

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

Rights & PermissionsPrintExport Cite as

Article Details

(E-pub Ahead of Print)
DOI: 10.2174/1570193X16666181204122143
Price: $95