Construction of Successive Stereogenic Centers of ent-Kauranoid via Oxidative Dearomatization/1,2-Shift Cascade
Construction of Successive Stereogenic Centers of ent-Kauranoid via Oxidative Dearomatization/1,2-Shift Cascade
复制标题
通过氧化脱芳构化/1,2-位移级联构建 ent-Kauranoid 的连续立体中心
DOI：
10.1055/a-1855-3777
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发表时间：
2022
期刊：
影响因子：
2
通讯作者：
Nakada Masahisa
中科院分区：
文献类型：
--
作者：
Imamura Yuki;Mizutani Hikaru;Nakada Masahisa
通过氧化脱芳构化/1，2-移位级联，连续的立体异构中心，包括一个全碳四元立体异构中心，often-贝壳杉烷的建设进行了描述。开发的带有atrans-2-（p-甲氧基苯基）乙烯基作为迁移基团的底物的级联反应以83%的产率得到了所需的产物。级联中的1，2-位移强烈地受到立体电子效应的影响。的X-射线晶体结构的化合物轴承四个连续的立体异构中心的稠环部分的对映贝壳杉烷二萜，这是由氧化脱芳构化/1，2-移位级联和随后的立体选择性转换，也报道。
The construction of the successive stereogenic centers, including an all-carbon quaternary stereogenic center, ofent-kauranoid through an oxidative dearomatization/1,2-shift cascade is described. The developed cascade reaction of a substrate bearing atrans-2-(p-methoxyphenyl)vinyl group as the migrating group afforded the desired product in 83% yield. The 1,2-shift in the cascade is strongly affected by a stereoelectronic effect. The X-ray crystal structure of a compound bearing four successive stereogenic centers in the fused-ring moiety ofent-kauranoid diterpene, which was prepared by the oxidative dearomatization/1,2-shift cascade and subsequent stereoselective transformations, is also reported.