Tetrahedron

Diastereospecific epoxidation and highly regioselective ring-opening of (+)-valienamine: practical synthesis of (+)-valiolamine

L Ji, D Zhang, Q Zhao, S Hu, C Qian, XZ Chen

Index: Ji, Li; Zhang, Ding-Feng; Zhao, Qian; Hu, San-Ming; Qian, Chao; Chen, Xin-Zhi Tetrahedron, 2013 , vol. 69, # 34 p. 7031 - 7037

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Citation Number: 8

Abstract

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. ...