Asymmetric Synthesis of (+)-Vellosimine Enabled by a Sequential Nucleophilic Addition/Cyclization Process

被引：3

作者：

Zou, Huanhuan ^{[1
]}

Yan, Jiahang ^{[1
]}

Zhang, Xiaocheng ^{[1
]}

Wu, Xiaohui ^{[1
]}

Huo, Jiyou ^{[1
]}

Xu, Yuanzhen ^{[1
]}

Xie, Weiqing ^{[1
,2
]}

机构：

[1] Northwest A&F Univ, Coll Chem & Pharm, Shaanxi Key Lab Nat Prod & Chem Biol, Yangling 712100, Shaanxi, Peoples R China

[2] Key Lab Bot Pesticide R&D Shaanxi Prov, Yangling 712100, Shaanxi, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 46期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSPECIFIC TOTAL-SYNTHESIS; INDOLE ALKALOIDS;

D O I：

10.1021/acs.orglett.3c03170

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we achieved the asymmetric synthesis of (+)-vellosimine in 13 steps (longest linear sequences, LLS). This synthesis featured a sequential nucleophilic addition/cyclization process, which provided an efficient protocol for synthesizing a range of indole fused azabicyclo[3.3.1]nonane. Additionally, a SmI2-mediated reductive cyclization of ketone with an attached alpha,beta-unsaturated ester for constructing the strained quinuclidine moiety was also highlighted.

引用

页码：8215 / 8219

页数：5

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