Concise synthesis of two advanced intermediates for the asymmetric synthesis of polyhydroxylated indolizidine alkaloids  

作　　者：ZHENG Xiao1,2,ZHU WenFang1 & HUANG PeiQiang1 1Department of Chemistry,College of Chemistry and Chemical Engineering,Xiamen University,Xiamen 361005,China 2Key Laboratory of Synthetic Chemistry of Natural Substances Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China 

出　　处：《Science China Chemistry》2010年第9期1914-1920,共7页中国科学（化学英文版）

基　　金：the National Natural Science Foundation of China (20832005);the National Basic Research Program (973 Program) of China (2010CB833200) for financial support

摘　　要：A concise five-step approach to indolizidinones 10 and 11,two advanced intermediates for the asymmetric synthesis of polyhydroxylated indolizidine alkaloids,has been developed by using N-Cbz pyrrolidin-2-yl pyridin-2-yl sulfide 13 as the chiral building block.The method features a SmI2-mediated coupling of sulfide 13 with functionalized aldehyde 14 and a tandem N-deprotection-lactamization,which constitutes a stepwise "2 + 4" annulation method for the construction of the indolizidinone ring system of 12a.A concise five-step approach to indolizidinones 10 and 11,two advanced intermediates for the asymmetric synthesis of polyhydroxylated indolizidine alkaloids,has been developed by using N-Cbz pyrrolidin-2-yl pyridin-2-yl sulfide 13 as the chiral building block.The method features a SmI2-mediated coupling of sulfide 13 with functionalized aldehyde 14 and a tandem N-deprotection-lactamization,which constitutes a stepwise "2 + 4" annulation method for the construction of the indolizidinone ring system of 12a.

关 键 词：indolizidinone SAMARIUM DIIODIDE α-amidohydroxyalkylation TANDEM reaction CHIRAL building block 

分 类 号：O621.34[理学—有机化学]