Asymmetric synthesis of the four stereoisomers of 5-deoxystrigol
Asymmetric synthesis of the four stereoisomers of 5-deoxystrigol
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DOI：
10.1016/j.tetlet.2014.10.040
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发表时间：
2014-11-26
影响因子：
1.8
通讯作者：
De Mesmaeker, Alain
中科院分区：
文献类型：
--
作者：
Lachia, Mathilde;Dakas, Pierre-Yves;De Mesmaeker, Alain
研究了用烯酮/酮亚胺与烯烃的环加成反应合成三环内酯骨架2的两种方法。最后，首次报道了通过高手性酮-亚胺盐5的分子内[2+2]环加成反应获得5-脱氧雌酚-1的四种立体异构体。以C-2对称的吡咯烷作为手性助剂，实现了很高的不对称控制。(C)2014爱思唯尔有限公司。保留所有权利。
Two approaches to the strigolactone tricyclic lactone skeleton 2 were investigated using ketene/keteneiminium cycloaddition to olefins. Finally, the first enantioselective access to the four stereoisomers of 5-deoxystrigol 1 is reported using an intramolecular [2+2] cycloaddition of homochiral ketene-iminium salts 5. Very high asymmetric control was achieved with C-2 symmetric pyrrolidines as chiral auxiliary. (C) 2014 Elsevier Ltd. All rights reserved.