Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5218641 | Tetrahedron | 2013 | 7 Pages |
Abstract
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.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Li Ji, Ding-feng Zhang, Qian Zhao, San-ming Hu, Chao Qian, Xin-Zhi Chen,