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

页码：743 / 745

页数：3

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