Efficient total synthesis of bastadin 6, an anti-angiogenic brominated tyrosine-derived metabolite from marine sponge
Efficient total synthesis of bastadin 6, an anti-angiogenic brominated tyrosine-derived metabolite from marine sponge
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DOI：
10.1016/j.tet.2005.05.038
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发表时间：
2005-07-25
期刊：
影响因子：
2.1
通讯作者：
Kobayashi, M
中科院分区：
文献类型：
--
作者：
Kotoku, N;Tsujita, H;Kobayashi, M
从海绵羊肚菌中高效地合成了具有选择性抗血管生成活性的溴化酪氨酸衍生物的环状四聚体--巴斯塔丁6(1)。我们建立了一种新型的Ce(IV)催化的2，6-二溴苯酚氧化偶联反应，得到了特征链段为1的二芳基醚衍生物。两段缩合和随后的分子内大环合得到了9步反应，总收率为26%。(C)2005爱思唯尔有限公司。保留所有权利。
An efficient total synthesis of bastadin 6 (1), a cyclic tetramer of brominated tyrosine derivatives from the marine sponge, lanthella basta, with selective anti-angiogenic activity, was accomplished. We developed a novel Ce(IV)-mediated oxidative coupling reaction of 2,6-dibromophenols to give the diaryl ether derivatives, the characteristic segment of 1. Condensation of two segments and subsequent intramolecular macrocyclization gave bastadin 6 (1) in nine steps, 26% overall yield. (c) 2005 Elsevier Ltd. All rights reserved.