Total synthesis of natural (-)- and unnatural (+)-Melearoride A

被引：8
|
作者：
Reed, Carson W. [1 ]
Fulton, Mark G. [1 ]
Nance, Kellie D. [1 ]
Lindsley, Craig W. [1 ,2 ]
机构：
[1] Vanderbilt Univ, Dept Chem, Nashville, TN 37232 USA
[2] Vanderbilt Univ, Dept Pharmacol, Vanderbilt Ctr Neurosci Drug Discovery, Nashville, TN 37232 USA
来源：
TETRAHEDRON LETTERS | 2019年 / 60卷 / 10期
关键词：
Melearoride A; Total synthesis; Macrolides; Asymmetric alkylation;
D O I：
10.1016/j.tetlet.2019.02.006
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This communication details the first total synthesis of the 13-membered macrolide, (-)-Melearoride A, as well as unnatural (+)-Melearoride A. The synthesis features a concise 13 step synthesis (11 steps longest linear sequence) that offers flexible stereo-control and multiple opportunities for unnatural analog synthesis to delve into antifungal SAR. The route features a cuprate addition, an Evans asymmetric alkylation, and a ring-closing metathesis (RCM) to close the 13-membered macrocyclic core. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码：743 / 745
页数：3
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