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

页码：4834 / 4837

页数：4

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