Synthesis of DMJ analogs with seven- and eight-membered iminocyclitols

TETRAHEDRON

卷:63

Article

Chang, Meng-Yang ; Kung, Yung-Hua ; Ma, Chih-Chong ; Chen, Shui-Tein

关键词: trans-(2S,4R)-4-hydroxyproline;    1-deoxymannojirimycin (DMJ);    azepane;    azocane;    Grignard addition;    ring-closing metathesis;    stereoselective osmylation;   

DOI  :  10.1016/j.tet.2006.12.002

来源: Elsevier

【 摘 要 】

A straightforward synthesis of new hydroxy azepane and azocane with an additional hydroxymethyl side arm (1-deoxymannojirimycin, DMJ analogs) has been achieved from trans-(2S,4R)-4-hydroxyproline via Grignard addition, ring-closing metathesis, and stereoselective osmylation as the key steps. (c) 2006 Elsevier Ltd. All rights reserved.

【 授权许可】

Free