A plausible chemical analogy for biosynthesis of 2-arylbenzofuran of isoflavonoid origin and its application to synthesis of vignafuran

✍ Scribed by Takeshi Kinoshita

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 237 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(96)02276-9

✦ Synopsis

Treatment of 2-hydroxy-isoflav-3-ene with acid afforded 2-arylbenzofuran in good yield, and a mechanism for this chemical conversion involving loss of one carbon unit was described. This reaction scheme was suggested as a plausible chemical analogy for the corresponding biosynthetic process of 2-arylbenzofuran of isoflavonoid origin, and a new biosynthetic scheme depicting 2-hydroxy-isoflav-3-ene as the possible common intermediate for both 2arylbcnzofuran and 3-aryleoumarin was proposed. Synthesis of a potent antimicrobial 2-arylbenzofuran pbytoalexin, vignafuran, was also achieved by use of this chemical scheme.