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SNAr Reaction/Claisen Rearrangement Approach to 2,4-Diisoprenylxanthones: Total Synthesis of Garcinone A
Synlett ( IF 1.7 ) Pub Date : 2020-06-09 , DOI: 10.1055/s-0040-1707819
Takashi Matsumoto , Miho Mochizuki , Yuuki Fujimoto , Hikaru Yanai

A total synthesis of garcinone A, a natural xanthone possessing a 2,4-diisoprenylated structure, was accomplished by utilizing a readily available 1,3-difluoroxanthone derivative as the key intermediate through the installation of two isoprenyl side chains by an SNAr reaction with the alkoxide of 1,1-dimethylallyl alcohol followed by a Claisen rearrangement. The strategy also permitted the selective installation of mutually different allylic moieties at the C2 and C4 positions.

中文翻译:

2,4-二异戊二烯基氧杂蒽酮的 SNAr 反应/克莱森重排方法:Garcinone A 的全合成

Garcinone A 的全合成是一种具有 2,4-二异戊二烯化结构的天然呫吨酮,它是通过利用容易获得的 1,3-二氟呫吨酮衍生物作为关键中间体,通过 SNAr 反应安装两个异戊二烯基侧链来完成的。 1,1-二甲基烯丙醇的醇盐,然后进行克莱森重排。该策略还允许在 C2 和 C4 位置选择性安装互不相同的烯丙基部分。
更新日期:2020-06-09
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