Tunable Cyclization Strategy for the Synthesis of Zizaene-, allo-Cedrane-, seco-Kaurane-, and seco-Atesane-Type Skeletons,Organic Letters

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Tunable Cyclization Strategy for the Synthesis of Zizaene-, allo-Cedrane-, seco-Kaurane-, and seco-Atesane-Type Skeletons
Organic Letters ( IF 4.9 ) Pub Date : 2017-09-21 00:00:00 , DOI: 10.1021/acs.orglett.7b02610
Qianqian Yang ₁ , Wenjing Ma ₁ , Gaopeng Wang ₁ , Wenli Bao ₁ , Xiaoshu Dong ₁ , Xuefeng Liang ₁ , Lizhi Zhu ₁ , Chi-Sing Lee ₁

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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.

中文翻译：

可调环化战略Zizaene-的合成，异体-Cedrane-，塞科-Kaurane-和塞科-Atesane型骨架

一种多功能路易斯酸介导的环化策略已经被开发用于选择性地建立zizaene-，同种异体-cedrane-，开环-kaurane-，和开环-atesane型骨架。的zizaene-和开环-atesane型骨架可以以级联的方式，它涉及与二甲硅烷氧基二烯和carbocyclization炔烯醇化物的通过路易斯酸依赖性5-或6-环烯酮的Diels-Alder反应来获得外切挖模式。这种环化策略也被用于tashironin的核心合成。

更新日期：2017-09-21

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