SNAr Reaction/Claisen Rearrangement Approach to 2,4-Diisoprenylxanthones: Total Synthesis of Garcinone A

被引：1
|
作者：
Mochizuki, Miho [1 ]
Fujimoto, Yuuki [1 ]
Yanai, Hikaru [1 ]
Matsumoto, Takashi [1 ]
机构：
[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan
来源：
SYNLETT | 2020年 / 31卷 / 15期
基金：
日本学术振兴会;
关键词：
natural product synthesis; xanthones; isoprenylation; SNAr reaction; Claisen rearrangement; garcinone A; PRENYLATED XANTHONES; IN-VITRO; ISOPRENYLATION; DERIVATIVES; PHARMACOLOGY; EXTRACTIVES; SELECTIVITY; GUTTIFERAE; POSITION;
D O I：
10.1055/s-0040-1707819
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：1511 / 1516
页数：6
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