Ti(III)-promoted cyclizations.: Application to the synthesis of (E)-endo-bergamoten-12-oic acids.: Moth oviposition stimulants isolated from Lycopersicon hirsutum
Ti(III)-promoted cyclizations.: Application to the synthesis of (E)-endo-bergamoten-12-oic acids.: Moth oviposition stimulants isolated from Lycopersicon hirsutum
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DOI：
10.1016/j.tet.2006.07.020
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发表时间：
2006-09-18
期刊：
影响因子：
2.1
通讯作者：
Rubio Gonzalez, Rosa
中科院分区：
文献类型：
--
作者：
Bermejo, Francisco A.;Fernandez Mateos, Alfonso;Rubio Gonzalez, Rosa
钛(111)促进的环氧酮8的自由基环化反应被描述为获得二元醇10作为目标分子的方便的起始原料的关键步骤。以(+)-8，9-环氧香芹酮8为原料，经Suzuki-Miyaura偶联、脱保护和脱水反应合成了β-(E)-内酯-佛手内酯-12-酸2a。此外，通过重复延长二醇10侧链的过程，合成了α-(E)-内-1-羟基-佛手内酯-12-酸衍生物34。(C)2006爱思唯尔有限公司。保留所有权利。
The Ti (111)-promoted radical cyclization of epoxyenone 8 is described as the key step to access the diol 10 as a convenient starting material of the target molecules. The synthesis of beta-(E)-endo-bergamoten-12-oic acid 2a from (+)-8,9-epoxycarvone 8 was successfully achieved by Suzuki-Miyaura coupling of the terminal alkene 20 with beta-iodomethacrylate 21c, followed by deprotection and dehydration processes. Moreover, synthesis of the alpha-(E)-endo-1-hydroxy-bergamoten-12-oic acid derivative 34 was achieved by iterative elongation processes of the diol 10 lateral chain. (c) 2006 Elsevier Ltd. All rights reserved.