A Formal Synthesis of (±)-Arborisidine

被引：4

作者：

Huo, Liang ^{[1
]}

Yang, Yunxia ^{[1
]}

Gao, Xiaofei ^{[1
]}

Chen, Wei ^{[1
]}

She, Xuegong ^{[1
]}

Cao, Xiao-Ping ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 18期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC TOTAL-SYNTHESIS; INDOLE ALKALOIDS; (+/-)-STRICTAMINE; STRICTAMINE; ALLYLATION; SKELETON;

D O I：

10.1021/acs.orglett.4c00928

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report a formal synthesis of (+/-)-arborisidine via the creation of Jiao's intermediate with the critical caged structure. Starting from tryptamine, a Pictet-Spengler cyclization forged the piperidine ring, a Pd-catalyzed indole allylation and ring-closing metathesis protocol afforded a bridged aza-bicyclo[3.3.1]nonane moiety, and an intramolecular N-alkylation closed the final pyrrolidine ring. This study provides a new approach to the unique caged framework of arborisidine and relevant alkaloids.

引用

页码：3801 / 3805

页数：5

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