Macrocycles by ring-closing-metathesis, XI:: Syntheses of (R)-(+)-lasiodiplodin, zeranol and truncated salicylihalamides
Macrocycles by ring-closing-metathesis, XI:: Syntheses of (R)-(+)-lasiodiplodin, zeranol and truncated salicylihalamides
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DOI：
10.1016/s0040-4020(99)00302-6
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发表时间：
1999-07-02
期刊：
影响因子：
2.1
通讯作者：
Kindler, N
中科院分区：
文献类型：
--
作者：
Fürstner, A;Seidel, G;Kindler, N
本文描述了一种简洁、灵活和高产的方法来合成欧芹酸型大环内酯类化合物lasiodiplodin 1和zeranol 3，这些方法只涉及金属辅助或金属催化的c -c键形成。关键步骤是通过Stille或改性Suzuki偶联反应对芳基三氟化酯14和25进行有效的烯丙化反应，并用RCM以钌18为催化剂对大环进行高收率的环闭合。其中一种合成中间体，即环烯烃16，也可视为强效抗肿瘤剂水杨柳卤酰胺a7的截断类似物。从16的体外细胞毒性数据可以推断出水杨柳卤酰胺结构/活性关系的第一个见解。1999爱思唯尔科学有限公司版权所有。
Concise, flexible and high yielding approaches to the orsellinic acid type macrolides lasiodiplodin 1 and zeranol 3 are described which involve only metal-assisted or metal-catalyzed C-C-bond formations. Key steps are the efficient allylation of aryl triflates 14 and 25 either by Stille or by modified Suzuki coupling reactions, and the high yielding ring closure of the macrocyclic rings by RCM using the ruthenium carbene 18 as the catalyst. One of the synthesis intermediates, i.e. cycloalkene 16, can also be regarded as a truncated analogue of the potent anti-tumor agent salicylihalamide A 7. From the in-vitro cytotoxicity data of 16 it is possible to deduce first insights into the structure/activity relationship of salicylihalamide. (C) 1999 Elsevier Science Ltd. All rights reserved.