The Synthesis Of (±)△~3, 2-hydroxybakuchiol And Its Analogues

Psoralea corylifolia L.is an annual plant of Fabaceae family and widely distributed in South China,India and Southeastern Asian countries.The whole extract or some of purified constituents from the plant have been reported to exhibit various biological activities such as antioxidant, anti-inflammatory,antitumor,and as well as the inhibitory effect on protein-tyrosine phosphatase-1B(PTP1B).Δ~3,2-hydroxybakuchiol,a component from the seed of Psoralea corylifolia L.,was first isolated in 1996 and identified in 1997.Up to most recently,it is disclosed to possess the promising inhibitory effect on dopamine transporter and dopamine reuptake,but few attention is paid to the natural product due to its scarcity and lability.In this article,we have provided a first access to prepare(±)Δ~3,2-hydroxybakuchiol and its analogues.In our approach to the natural product,the key steps are Claisen rearrangement,Takai olefination and Negishi coupling reaction.Thus(±)-Δ~3,2-hydroxybakuchiol could be obtained in 12 steps and in overall yield of 9.4%by the approach.The same approach will also be applied for the syntheses of the divergent compounds in order to investigate the further structure activity relationship of dopamine transporter inhibition and relative biological study.