Asymmetric synthesis of pedamide using I_2-induced heterocyclization to construct the skeleton  

作　　者：De Gang Liu Ji Jun Xue Zhi Xiang Xie Li Ping Wei Hua Bing Zhang Ying Li 

机构地区：[1]State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China

出　　处：《Chinese Chemical Letters》2009年第7期775-778,共4页中国化学快报（英文版）

基　　金：the financial support of the National Natural Science Foundation of China(No.20672050).

摘　　要：An alternative approach to synthesize pedamide, a key building block of pederin was described. Iodine-induced asymmetric heterocyclization was used as the key step to construct the skeleton, a tetrahydropyran ring with three chiral centers. Brown＇s asymmetric allylation and Lewis acid-mediated allylation were investigated to introduce chains and chiral alcohols. Sharpless dihydroxylation decorated the side chain. And high optically pure target was obtained by removing the epimers formed in these reactions on column chromatography.C2009 Ji Jun Xue. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All fights reserved.An alternative approach to synthesize pedamide, a key building block of pederin was described. Iodine-induced asymmetric heterocyclization was used as the key step to construct the skeleton, a tetrahydropyran ring with three chiral centers. Brown＇s asymmetric allylation and Lewis acid-mediated allylation were investigated to introduce chains and chiral alcohols. Sharpless dihydroxylation decorated the side chain. And high optically pure target was obtained by removing the epimers formed in these reactions on column chromatography.C2009 Ji Jun Xue. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All fights reserved.

关 键 词：SYNTHESIS Pedamide Pederin 

分 类 号：O621.34[理学—有机化学] TP391.41[理学—化学]