Synthesis of Racemic Δ3-2-Hydroxybakuchiol and Its Analogues

✍ Scribed by Lei Shi; Xinsheng Lei; Jiange Zhang; Guoqiang Lin

• Book ID: 102254579
• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: German
• Weight: 213 KB
• Volume: 93
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200900243

✦ Synopsis

Abstract

The first synthetic approach to (±)‐Δ^3^‐2‐hydroxybakuchiol (=4‐[(1__E__,5__E__)‐3‐ethenyl‐7‐hydroxy‐3,7‐dimethylocta‐1,5‐dien‐1‐yl]phenol; 14) and its analogues 13a–13f was developed by 12 steps (Schemes 2 and 3). The key features of the approach are the construction of the quaternary C‐center bearing the ethenyl group by a Johnson–Claisen rearrangement (→6); and of an (E)‐alkenyl iodide via a Takai–Utimoto reaction (→11); and an arylation via a Negishi cross‐coupling reaction (→12e–12f).