1020108-62-6Relevant articles and documents
A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol and ent-Bakuchiol
Xu, Qian-Qian,Zhao, Qun,Shan, Guang-Sheng,Yang, Xi-Cheng,Shi, Qi-Yuan,Lei, Xinsheng
, p. 10739 - 10746 (2013/12/04)
A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol, and ent-Bakuchiol is described through one common intermediate bearing a chiral all-carbon quaternary carbon center, which involves stereoselectively unconjugated alkylation of the α,β-unsaturated imide bearing Evans' auxiliary, Takai-Utimoto reaction, Negishi reaction, and Heck reaction as key steps.
Stereoselective total synthesis of natural (S)-bakuchiol and its enantiomer
Du, Xiao-Long,Chen, Hong-Li,Feng, Hui-Jin,Li, Yuan-Chao
experimental part, p. 371 - 378 (2009/02/07)
A practical stereoselective synthesis of (S)-bakuchiol (1) and its enantiomer is reported. The important intermediate, (R)-configured β-siloxy aldehyde 5, was obtained in three steps from the easily available material geraniol (2) via the key step of Yamamoto's rearrangement of epoxy silyl ethers. (S)-Bakuchiol (1) and its enantiomer, (R)-bakuchiol (17), were finally obtained in different synthetic sequences with overall yields of 51% (ten steps) and 40% (nine steps) from geraniol (2), respectively.