1447971-22-3Relevant academic research and scientific papers
Diastereospecific epoxidation and highly regioselective ring-opening of (+)-valienamine: Practical synthesis of (+)-valiolamine
Ji, Li,Zhang, Ding-Feng,Zhao, Qian,Hu, San-Ming,Qian, Chao,Chen, Xin-Zhi
, p. 7031 - 7037 (2013)
An efficient and practical synthesis of (+)-valiolamine starting from readily available aminocyclitol (+)-valienamine in five steps and up to 80% total yield in gram-scale quantities is reported. Diastereospecific epoxidation by means of substrate directable reaction and regioselective ring-opening of corresponding epoxide are the key reactions in the synthesis, which circumvent laborious purification of products using chromatographical separation. The detailed mechanisms of epoxidation and ring-opening attacked by halide, including the directing and steric hindrance effect, are also discussed.
