Total Syntheses of Cochliomycin B and Zeaenol

Total Syntheses of Cochliomycin B and Zeaenol
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Cochliomycin B 和玉米烯醇的全合成

DOI:
10.1002/ejoc.201301613
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发表时间:
2014-04-01
影响因子:
2.8
通讯作者:
Du, Yuguo
Du, Yuguo
中科院分区:
化学3区
文献类型:
--
作者:
Gao, Yangguang;Liu, Jun;Du, Yuguo

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两种14元环的间苯二酚酸内酯(RALs),即卷曲霉素B(6)和玉米赤霉烯醇(22)的发散性合成已经完成。我们策略的关键特点是利用天然的L - 阿拉伯糖作为手性模板,简便地构建了标题分子中三个连续的手性中心。关键反应包括高井烯化反应、铃木交叉偶联反应、酯交换反应以及后期的关环复分解反应(RCM)。
Divergent syntheses of two 14-membered resorcylic acid lactones (RALs), cochliomycin B (6) and zeaenol (22), have been accomplished. The key feature in our strategy was the facile construction of three contiguous stereogenic centers in the title molecules by using natural L-arabinose as the chiral template. The key reactions included Takai olefination, Suzuki cross coupling, transesterification, and a late-stage ring-closing metathesis (RCM).