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

页码：18642 / 18648

页数：7

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