Premium
Kinetic Resolution of Diols via Etherification Catalyzed by a Chiral Phosphoric Acid: Concise Synthesis of (+)‐Sacidumlignan D
Author(s) -
Xie Changmin,
Bai Donghu,
Huang ShaHua,
Jia Xueshun,
Hong Ran
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300250
Subject(s) - chemistry , kinetic resolution , phosphoric acid , tetrahydrofuran , catalysis , diol , organic chemistry , zinc , resolution (logic) , enantioselective synthesis , combinatorial chemistry , artificial intelligence , solvent , computer science
A kinetic resolution of a diol via etherification catalyzed by a chiral phosphoric acid was developed and applied in the concise total synthesis of (+)‐sacidumlignan D, the antipode of natural sacidumlignan D. A zinc‐mediated crotylation of a diarylketone and subsequent lactonization quickly established the carbon framework of this class of tetrahydrofuran lignans.