Model studies for the stereoselective construction of the BC-ring of armatol F based on Ireland-Claisen rearrangement and relay ring-closing olefin metathesis
Model studies for the stereoselective construction of the BC-ring of armatol F based on Ireland-Claisen rearrangement and relay ring-closing olefin metathesis
复制标题
DOI：
10.1016/j.tetlet.2010.06.103
复制
发表时间：
2010-08-25
影响因子：
1.8
通讯作者：
Suzuki, Takanori
中科院分区：
文献类型：
--
作者：
Fujiwara, Kenshu;Tanaka, Keita;Suzuki, Takanori
Armatol F是一种从红色植物Chondria armata中分离出来的聚醚三萜，具有一个稠合的三环醚部分（BCD-环），在C-和D-环之间的C18-C19处有一个不寻常的顺式环连接。在armatol F的全合成过程中，通过合成单环（C-环）和双环（BC-环）模型化合物，建立了通过Ireland-Claisen重排立体选择性地构建C18和C19立构中心以及通过中继闭环烯烃复分解形成C-环。(C)2010爱思唯尔有限公司保留所有权利。
Armatol F, isolated from the red alga Chondria armata as a polyether triterpene, has a fused tricyclic ether moiety (BCD-ring) with an unusual cis ring junction at C18-C19 between the C- and D-rings. En route to the total synthesis of armatol F, the stereoselective construction of the C18 and C19 stereocenters by Ireland-Claisen rearrangement and the formation of the C-ring by relay ring-closing olefin metathesis were established through the synthesis of monocyclic (C-ring) and bicyclic (BC-ring) model compounds. (C) 2010 Elsevier Ltd. All rights reserved.