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

页码：1511 / 1516

页数：6

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