1226876-85-2Relevant academic research and scientific papers
Synthesis of racemic Δ3-2-hydroxybakuchiol and its analogues
Shi, Lei,Lei, Xinsheng,Zhang, Jiange,Lin, Guoqiang
experimental part, p. 555 - 564 (2010/06/14)
The first synthetic approach to (±)-Δ3-2- hydroxybakuchiol (=4-[(1E,5E)-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).
