First total synthesis of aerucyclamide B

被引：17
作者：
Pena, Stella [1 ]
Scarone, Laura [1 ]
Manta, Eduardo [1 ]
Serra, Gloria [1 ]
机构：
[1] Univ Republica, Fac Quim, Catedra Quim Farmaceut, Montevideo 11800, Uruguay
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 22期
关键词：
Aerucyclamide; Macrocyclization; Oxa(thia)zole; Hexacyclopeptide; MICROCYSTIS-AERUGINOSA; SECONDARY METABOLITES; CYCLIC-PEPTIDES; DEOXO-FLUOR; CYANOBACTERIA; CYCLIZATION; OXAZOLINES; THIAZOLINES; INHIBITORS; ANALOGS;
D O I：
10.1016/j.tetlet.2013.03.060
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first total synthesis of the antimalarial aerucyclamide B has been achieved in 9% overall yield. Two thiazoles and a dipeptide were used to prepare two open precursors of cyclo-Gly-L-allo-Thr-L-Ile-Thz-D-allo-Ile-Thz. Cyclodehydration with Deoxo-Fluor of the beta-hydroxyamide present in the macrocycle, rendered aerucyclamide B (67%) and an unexpected fluorous derivative (28%). (C)13 Elsevier Ltd. All rights reserved.
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页码：2806 / 2808
页数：3
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