Formal syntheses of (±)-Asterisca-3(15),6-diene and (±)-Pentalenene using Rh(I)-catalyzed [(5+2)+1] cycloaddition
Formal syntheses of (±)-Asterisca-3(15),6-diene and (±)-Pentalenene using Rh(I)-catalyzed [(5+2)+1] cycloaddition
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DOI：
10.1016/j.tet.2009.04.020
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发表时间：
2009-06-13
期刊：
影响因子：
2.1
通讯作者：
Yu, Zhi-Xiang
中科院分区：
文献类型：
--
作者：
Fan, Xiaohui;Zhuo, Lian-Gang;Yu, Zhi-Xiang
具有双环[6.3.0]十一烷骨架的天然产物(+/-)-Asterisca-3(15)，6-二烯和(+/-)-戊烯的有效形式合成。通过Rh(I)催化的[(5+2)+1]环加成反应，得到了具有三环[6.3.0.0(4，8)]十一烷骨架的天然产物。[(5+2)+1]反应提供了一种快速合成双环环辛烯酮4的方法，该双环辛烯酮4通过氢化硼然后氧化快速转化为二酮14，这是全合成(+/-)-Asterisca-3(15)，6-二烯的关键高级中间体。通过进一步的转化，14被转化为二烯18，这是一种用于全合成(+/-)-戊烯的高级中间体。(C)2009爱思唯尔有限公司。保留所有权利。
Efficient formal syntheses of (+/-)-Asterisca-3(15),6-diene, a natural product with a bicyclo[6.3.0]undecane skeleton, and (+/-)-Pentalenene. a natural product with a tricyclo[6.3.0.0(4,8)]undecane skeleton, have been achieved by using Rh(I)-catalyzed [(5+2)+1] cycloaddition. The [(5+2)+1] reaction provides an expeditious approach to reach the bicyclic cyclooctenone 4, which was quickly transformed (via hydroboration then oxidation) to diketone 14, a key advanced intermediate for the total synthesis of (+/-)-Asterisca-3(15),6-diene. Through further transformations, 14 was converted to diene 18, an advanced intermediate for the total synthesis of (+/-)-Pentalenene. (C) 2009 Elsevier Ltd. All rights reserved.