Synthesis of fully protected (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxy heptanoic acid

被引:3
作者
Yoshino, Ryo [1 ]
Tokairin, Yoshinori [1 ]
Konno, Hiroyuki [1 ]
机构
[1] Yamagata Univ, Grad Sch Sci & Engn, Dept Biol Engn, Yonezawa, Yamagata 9928510, Japan
基金
日本学术振兴会;
关键词
Unusual amino acid; Callipeltins; Guanidination; Arginine derivative; SOLID-PHASE SYNTHESIS; SPONGE LATRUNCULIA SP; CALLIPELTIN-A; CYCLIC DEPSIPEPTIDES; CYCLODEPSIPEPTIDE; DERIVATIVES; AGDHE; (2R; 3R;
D O I
10.1016/j.tetlet.2017.03.025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(2R,3R,4S)-4-Amino-7-guanidino-2,3-dihydroxyheptanoic acid (AGDHE), a common constituent of biologically active marine peptides, callipeltin A (1) and neamphamide A, was synthesized as its orthogonally protected derivative from L-glutamic acid in 15 steps. Guanidination by the Mitsunobu condition and osmium-catalyzed dihydroxylation of the corresponding Z-olefin were employed as the key steps. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1604 / 1606
页数:3
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