Asymmetric Synthesis of Dihydrospirotryprostatin B via a Silica Gel-Mediated Cyclization of Tryptamine-Ynamide

被引：0

作者：

Han, Changhong ^{[1
,2
,3
]}

Yang, Lu ^{[1
,2
,3
]}

Yao, Kaizong ^{[1
,2
,3
]}

Zhang, Sen ^{[1
,2
,3
]}

Fu, Jiayue ^{[1
,2
,3
]}

Sun, Hanyang ^{[1
,2
,3
]}

Xu, Hongsheng ^{[4
]}

Lin, Bin ^{[1
,2
,3
]}

Cheng, Maosheng ^{[1
,3
]}

Liu, Yongxiang ^{[1
,2
,3
]}

机构：

[1] Shenyang Pharmaceut Univ, Key Lab Struct Based Drug Design & Discovery, Minist Educ, Shenyang 110016, Liaoning, Peoples R China

[2] Shenyang Pharmaceut Univ, Wuya Coll Innovat, Shenyang 110016, Liaoning, Peoples R China

[3] Inst Drug Res Med Capital China, Benxi 117000, Liaoning, Peoples R China

[4] Zhejiang Shapuaisi Pharmaceut Co Ltd, Hangzhou 314299, Zhejiang, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2024年 / 42卷 / 12期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

Asymmetric synthesis; Alkaloids; Dihydrospirotryprostatin B; Tryptamine-ynamide; Cross-coupling; Silica gel-mediated cyclization; Oxidation; MAMMALIAN-CELL CYCLE; SPIROTRYPROSTATIN-B; ASPERGILLUS-FUMIGATUS; TANDEM CYCLIZATIONS; CONCISE; (-)-SPIROTRYPROSTATIN-B; INHIBITORS;

D O I：

10.1002/cjoc.202300727

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An asymmetric synthesis of dihydrospirotryprostatin B was achieved in 15 steps (8 purifications) from L-tryptophan. The main feature of our synthetic strategy is the efficient construction of spirocyclic oxindole intermediate containing a chiral quaternary carbon center, involving the silica gel-mediated cyclization of tryptamine-ynamide and oxidation under neat conditions.

引用

页码：1355 / 1359

页数：5

共 41 条

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