Studies towards an Enantioselective Total Synthesis of Sarain A: A Concise Asymmetric Construction of the Diazatricyclic Core

被引：31
|
作者：
Yang, Rui-Feng [1 ,2 ]
Huang, Pei-Qiang [1 ,2 ,3 ]
机构：
[1] Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Fujian, Peoples R China
[2] Xiamen Univ, Key Lab Chem Biol Fujian Prov, Coll Chem & Chem Engn, Xiamen 361005, Fujian, Peoples R China
[3] State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 34期
关键词：
alkaloids; asymmetric synthesis; cyclization; Michael addition; Sarain A; total synthesis; STEREOCONTROLLED SYNTHESIS; HYDROXYLATED PYRROLIDINES; TRICYCLIC CORE; N-DEALKYLATION; ALKALOIDS; PRECURSORS; CHEMISTRY;
D O I：
10.1002/chem.201001582
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Figure Presented A powerful chiral building block: A concise enantioselective synthesis of the diazatricyclic core of sarain A has been accomplished. The novel strategy relies upon the versatile chiral building block (R)-1(see scheme), and features a tandem Horner-WadsworthEmmons-aza-Michael reaction, an intramolecular Michael reaction, and the diastereoconvergent formation of the third ring. Diazatricyclic core 2 possesses all of the necessary functionality for further elaboration into sarain A. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：10319 / 10322
页数：4
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