Silver-Catalyzed Asymmetric Synthesis of 2,3-Dihydrobenzofurans: A New Chiral Synthesis of Pterocarpans

✍ Scribed by Leticia Jiménez-González; Sergio García-Muñoz; Miriam Álvarez-Corral; Manuel Muñoz-Dorado; Ignacio Rodríguez-García

• Book ID: 101833214
• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 182 KB
• Volume: 12
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200600332

✦ Synopsis

Abstract

2,3‐Dihydrobenzofurans can be diastereoselectively prepared by condensation of aromatic aldehydes with 2,3‐dihydrobenzoxasilepines under the catalysis of Ag^I^ complexes, and in the presence of a source of fluoride ion. The application of this strategy by using chiral catalysts leads to a new enantioselective total synthesis of natural cis‐pterocarpans and their trans isomers. Through this method, the first enantioselective total synthesis of the antifungal agent (−)‐pterocarpin was achieved. In addition, a new entry into the heteroaromatic system of 2,5‐dihydrobenzoxepine is also presented.