New Synthetic Routes to Biologically Interesting Geranylated Flavanones and Geranylated Chalcones: First Total Synthesis of (±)-Prostratol F, Xanthoangelol, and (±)-Lespeol

✍ Scribed by Doo Hwan Jung; Yong Rok Lee; Sung Hong Kim

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: German
• Weight: 255 KB
• Volume: 93
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200900251

✦ Synopsis

Abstract

A new and efficient synthetic approach to biologically interesting geranylated flavanones and geranylated chalcones is described. Thus, the first total syntheses of the geranylated flavanones (±)‐prostratol F (1), (±)‐8‐geranyl‐3′,4′,7‐trihydroxyflavanone (2), and (±)‐6‐geranyl‐5,7‐dihydroxy‐3′,4′‐dimethoxyflavanone (3) were carried out starting from 2,4‐dihydroxyacetophenone (10) and 2,4,6‐trihydroxyacethophenone (17) in five to six steps (Schemes 2 and 3). The geranylated chalcones xanthoangelol (4), 3‐geranyl‐2,3′,4,4′‐tetrahydroxychalcone (5), (±)‐lespeol (6), and lespeol derivatives (±)‐7–9 were synthesized starting from 2,4‐dihydroxyacetophenone (10) in three to four steps (Schemes 2 and 6).