31560-19-7Relevant articles and documents
Synthesis of (1R,4R)-2,5-diazabicyclo[2.2.1]heptane derivatives by an epimerization-lactamization cascade reaction
Cui, Benqiang,Yu, Jie,Yu, Fu-Chao,Li, Ya-Min,Chang, Kwen-Jen,Shen, Yuehai
, p. 10386 - 10392 (2015/01/30)
An epimerization-lactamization cascade of functionalized (2S,4R)-4-aminoproline methyl esters is developed and applied in synthesizing (1R,4R)-2,5-diazabicyclo[2.2.1]heptane (DBH) derivatives. (2S,4R)-4-Aminoproline methyl esters are likely to undergo 2-epimerization under basic conditions, followed by an intramolecular aminolysis of the (2R)-epimer to form the bridged lactam intermediates. Key factors identified for this cascade reaction include the electron-withdrawal N-protective group in the substrates and a strong base as the promoter.
A concise formal synthesis of unnatural (+)-aphanorphine from (2S,4R)-4-hydroxyproline
Ma, Zhiqiang,Zhai, Hongbin
, p. 161 - 163 (2008/03/13)
(-)-Aphanorphine methyl ether was synthesized in ten steps from commercially available (2S,4R)-4-hydroxyproline, featuring the C-2 configuration inversion of an intermediate amide and intramolecular Friedel-Crafts reaction. The present work constitutes a
A concise approach to kainoid analogues
Baldwin, Jack E.,Rudolph, Martin
, p. 6163 - 6166 (2007/10/02)
Highly neuroexcitatory kainoid analogues bearing an aryl substituent at C-4 were synthesised by a short and efficient route from trans-L-4-hydroxypyroline.
