New Approach for the Construction of the Coumarin Frame and Application in the Total Synthesis of Natural Products

✍ Scribed by Alberto Jerezano; Fabiola Jiménez; María del Carmen Cruz; Luisa E. Montiel; Francisco Delgado; Joaquín Tamariz

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: German
• Weight: 235 KB
• Volume: 94
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.201000306

✦ Synopsis

A new synthetic approach is described for building the coumarin scaffold through the Lewis acidpromoted cyclization of novel aryl 3-(dimethylamino)prop-2-enoates 2a -2f. The latter precursors were prepared via aminomethylenation of the corresponding aryl acetates 4a -4f with the Bredereck reagent. This approach was used for the synthesis of biologically active natural compounds 1a -1f, through a three-step procedure starting from the corresponding phenols. Scheme 1. Proposed Synthetic Route