Studies toward the total synthesis of armatol F: stereoselective construction of the C6 and C7 stereocenters and formation of the A-ring skeleton
Studies toward the total synthesis of armatol F: stereoselective construction of the C6 and C7 stereocenters and formation of the A-ring skeleton
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DOI：
10.1016/j.tetlet.2010.06.026
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发表时间：
2010-08-11
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;Hirose, Yuta;Suzuki, Takanori
Armatol F是一种从红色植物Chondria armata中分离得到的聚醚三萜，具有一个单独的氧杂环庚烷（A-环）和一个稠合的三环醚部分（BCD-环）。A环的特点是季碳C6上的羟基和C7上的碳链之间存在罕见的顺式关系。作为我们的计划的一部分，对全合成阿马醇F，一个新的立体选择性的方法的建设的C6和C7立体中心已开发的基础上手性转移Ireland-Claisen重排。A-环骨架也已经由重排产物通过包括闭环烯烃复分解的方法合成。(C)2010爱思唯尔有限公司版权所有。
Armatol F, isolated from the red alga Chondria armata as a polyether triterpene, has a solitary oxepane (A-ring) and a fused tricyclic ether moiety (BCD-ring). The A-ring features a rare cis-relationship between the hydroxy group at the quaternary carbon C6 and the carbon chain at C7. As part of our program toward the total synthesis of armatol F, a new stereoselective method for the construction of the C6 and C7 stereocenters has been developed based on chirality-transferring Ireland-Claisen rearrangement. The A-ring skeleton has also been synthesized from the rearrangement product by a process including ring-closing olefin metathesis. (C) 2010 Elsevier Ltd. All rights reserved.