220300-07-2Relevant articles and documents
First total synthesis of Boehmenan
Xia, Yamu,Dai, Xiaoli,Liu, Haixin,Chai, Chen
, p. 813 - 820 (2014/07/07)
The first total synthesis of dilignan Boehmenan has been achieved. A biomimetic oxidative coupling of the ferulic acid methyl ester in the presence of silver oxide is the crucial step in the synthesis sequence, generating the dihydrobenzofuran skeleton. Hydroxyl group was protected with DHP and reducted with LiAlH 4 to afford the intermediate diol. The diol was condensated with the derivative of ferulic acid, then removed the protecting groups, to get Boehmenan. Meanwhile, a study on the ring-opening reaction of the intermediate dihydrobenzofuran neolignan under base conditions was described.
Facile one-pot transformation of 2,3-epoxy alcohols into allylic alcohols: First total synthesis of (-)-4-O-(6'-hydroxy- 7'(9')-dehydro- 6',7'-dihydrogeranyl)coniferol
Liu, Zuosheng,Lan, Jiong,Li, Yulin
, p. 3755 - 3762 (2007/10/03)
An efficient and practical synthesis of optically active allylic alcohols from 2,3-epoxy alcohols by the in situ formation of the epoxy iodides and their subsequent reduction with phosphine hydroxyiodide has been established. Using this reaction as the key step, we synthesized (-)-4-O- (6'-hydroxy-7'(9')-dehydro-6',7'-dihydrogeranyl)coniferol.