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

• Published in: Helvetica chimica acta Vol. 93; no. 4; pp. 635 - 647
• Main Authors: Jung, Doo Hwan, Lee, Yong Rok, Kim, Sung Hong
• Format: Journal Article
• Language: English
• Published: Zürich WILEY-VCH Verlag 01.04.2010; WILEY‐VCH Verlag; Wiley
• Subjects: Chalcones; Chalcones, geranylated; Chemistry; Chemistry, Multidisciplinary; Flavanones; Flavanones, geranylated; geranylated; Lespeol; Physical Sciences; Prostratol F; Science & Technology; Xanthoangelol; 4-HYDROXYDERRICIN; ARTOCARPUS-NOBILIS; ANTIMETASTATIC ACTIVITIES; LESPEDEZA-CYRTOBOTRYA; ROOTS; FLAVONOIDS; DERIVATIVES; PAULOWNIA-TOMENTOSA; ANGELICA-KEISKEI KOIDZUMI; CONSTITUENTS
• ISSN: 0018-019X; 1522-2675
• DOI: 10.1002/hlca.200900251

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).