Tunable Cyclization Strategy for the Synthesis of Zizaene-, allo-Cedrane-, seco-Kaurane-, and seco-Atesane-Type Skeletons.
Tunable Cyclization Strategy for the Synthesis of Zizaene-, allo-Cedrane-, seco-Kaurane-, and seco-Atesane-Type Skeletons.
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DOI：
10.1021/acs.orglett.7b02610
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发表时间：
2017-09
期刊：
影响因子：
5.2
通讯作者：
Qianqian Yang;Wenjing Ma;Gaopeng Wang;Wenli Bao;Xiaoshu Dong;Xuefeng Liang;Lizhi Zhu;Chi-Sing Lee
中科院分区：
文献类型：
--
作者：
Qianqian Yang;Wenjing Ma;Gaopeng Wang;Wenli Bao;Xiaoshu Dong;Xuefeng Liang;Lizhi Zhu;Chi-Sing Lee
一种多功能Lewis酸介导的环化策略已经被开发出来，用于选择性地建立zizaene-， alloo -雪松烷-，seco-kaurane-和seco-atesane型骨架。环烯酮与双硅氧基二烯的diols - alder反应和炔烯醇酯通过Lewis酸依赖的5-或6-外显子模式的碳环化反应可通过级联的方式获得齐辛烯和二辛烯型骨架。该环化策略也被用于塔什铁素的核心合成。
A versatile Lewis acid-mediated cyclization strategy has been developed for selectively establishing zizaene-, allo-cedrane-, seco-kaurane-, and seco-atesane-type skeletons. The zizaene- and seco-atesane-type skeletons can be obtained in a cascade manner, which involves Diels-Alder reaction of cyclic enones with bis-silyloxy dienes and carbocyclization of yne-enolates through Lewis acid dependent 5- or 6-exo-dig modes. This cyclization strategy was also employed for the core synthesis of tashironin.