An enantioselective synthesis of the C3-C21 segment of the macrolide immunosuppressive agent FR252921

被引：7
|
作者：
Ghosh, Arun K. [1 ]
Rodriguez, Samuel
机构：
[1] Purdue Univ, Dept Chem, 560 Oval Dr, W Lafayette, IN 47907 USA
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 26期
基金：
美国国家卫生研究院;
关键词：
FR252921; Macrolide; Synthesis; Immunosuppressive; Asymmetric; Aldol reaction; Asymmetric reduction; FLUORESCENS NO. 408813; PROMISING IMMUNOSUPPRESSANT; CYCLOSPORINE-A; ACID-B; REDUCTION; INHIBITOR; KETONES; ROUTE;
D O I：
10.1016/j.tetlet.2016.05.067
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An enantioselective synthesis of the C3-C21 segment of the novel immunosuppressant FR252921 is described. The C12 and C13 stereogenic centers were constructed by a non-aldol process utilizing optically active 4-phenylbutyrolactone. The C18 stereogenic center was installed using Braun's highly diastereoselective acetate aldol reaction. Other key steps involved Curtius rearrangement and Horner-Wadsworth-Emmons olefination reactions. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2884 / 2887
页数：4
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