Divergent Total Syntheses of Illicium Sesquiterpenes through Late-Stage Skeletal Reorganization

被引：9
|
作者：
Fu, Pengfei [1 ]
Liu, Tao [1 ]
Shen, Yang [1 ]
Lei, Xin [1 ]
Xiao, Tianjie [1 ]
Chen, Peng [1 ]
Qiu, Dongsheng [1 ]
Wang, Zhen [1 ]
Zhang, Yandong [1 ]
机构：
[1] Xiamen Univ, Coll Chem & Chem Engn, State Key Lab Phys Chem Solid Surfaces, Key Lab Chem Biol Fujian Prov,iCHEM, Xiamen 361005, Fujian, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2023年 / 145卷 / 33期
基金：
中国国家自然科学基金;
关键词：
PREZIZAANE-TYPE SESQUITERPENES; NEUROTROPHIC ACTIVITY; ENANTIOSPECIFIC SYNTHESIS; CHEMISTRY; ANALOGS;
D O I：
10.1021/jacs.3c06442
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We disclose unified, protecting-group-free, bioinspireddivergenttotal syntheses of eight allo-cedrane and seco-prezizaane Illicium sesquiterpenesand formal syntheses of five anislactone sesquiterpenes. The efficiencyof our approach derives from rapid access to the 15-carbon tricycliccarboxylic acid through cationic epoxide-ene cyclization and HAT oxygenation,transformation of this intermediate into three distinct tricyclicprecursors via Lewis acid-mediated skeletal reorganizations, subsequentprogrammed oxidation level enhancement, and a biomimetic oxidation-initiatedskeletal rearrangement cascade. Consequently, we created a syntheticcorrelation map of the three most prevalent Illicium sesquiterpene families.
引用
收藏
页码：18642 / 18648
页数：7
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