A Formal Enantioselective Total Synthesis of FR901483

被引：36
|
作者：
Huo, Hao-Hua [1 ]
Zhang, Hong-Kui [1 ]
Xia, Xiao-Er [1 ]
Huang, Pei-Qiang [1 ,2 ]
机构：
[1] Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Fujian, Peoples R China
[2] State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 18期
关键词：
POTENT IMMUNOSUPPRESSANT FR901483; STEREOCONTROLLED TOTAL-SYNTHESIS; MANNICH CYCLIZATION APPROACH; REDUCTIVE ALKYLATION; ASYMMETRIC-SYNTHESIS; TRICYCLIC SKELETON; RING-SYSTEM; IMINIUM ION; CORE; (-)-FR901483;
D O I：
10.1021/ol302165d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A formal enantioselective total synthesis of the potent immunosuppressant FR901483 (1) has been accomplished. Our approach features the use of chiron 6 as the starting material, the application of the one-pot amide reductive bisalkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diastereoselective intramolecular aldol reaction to build the bridged ring, and ring closing metathesis to form the 3-pyrrolin-2-one ring.
引用
收藏
页码：4834 / 4837
页数：4
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