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

Bracher, Franz (2020): Dimethylformamide Acetals and Bredereck's Reagent as Building Blocks in Natural Products Total Synthesis. In: Mini-Reviews in Organic Chemistry, Vol. 17, No. 1: pp. 47-66

Abstract

Dimethylformamide acetals and Bredereck's reagent (tert-butoxy-bis(dimethylamino) methane) are versatile C-1 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.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Pharmacy
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1570-193X
• Language: English