Synthesis of (-)-xialenon A by enantioselective α-deprotonation-rearrangement of a meso-epoxide
Synthesis of (-)-xialenon A by enantioselective α-deprotonation-rearrangement of a meso-epoxide
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DOI：
10.1016/j.tet.2003.09.023
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发表时间：
2003-12-01
期刊：
影响因子：
2.1
通讯作者：
Christlieb, M
中科院分区：
文献类型：
--
作者：
Hodgson, DM;Galano, JM;Christlieb, M
首次通过有机锂/(-)-α-异孕酮化合物对取代的环氧环烯进行对映选择性跨环去对称化反应，实现了(-)-夏洛烯A的全合成。氧化得到的双环[3.3.0]辛醇得到一个烯酮，它经历了立体选择性的共轭烯丙基化；随后在衍生的烯酮的更受阻碍的面上利用高价碘化学进行α‘-羟基化，得到了天然产物。(C)2003爱思唯尔有限公司。保留所有权利。
The first total synthesis of (-)-xialenon A was achieved via enantioselective transannular desymmetrisation of a substituted cycloctene oxide using an organolithium/(-)-alpha-isosparteine combination. Oxidation of the resulting bicyclo[3.3.0]octanol gave an enone which underwent stereoselective conjugate allylation; subsequent alpha'-hydroxylation on the more hindered face of a derived enone using hypervalent iodine chemistry led to the natural product. (C) 2003 Elsevier Ltd. All rights reserved.