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

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外文摘要：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.

外文关键词：

Asymmetric synthesisAlkaloidsDihydrospirotryprostatin BTryptamine-ynamideCross-couplingSilica gel-mediated cycliza-tionOxidation

作者：

Changhong Han、Lu Yang、Kaizong Yao、Sen Zhang、Jiayue Fu、Hanyang Sun、Hongsheng Xu、Bin Lin、Maosheng Cheng、Yongxiang Liu

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作者单位：

Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education,Shenyang Pharmaceutical University,Shenyang,Liaoning 110016,China

Wuya College of Innovation,Shenyang Pharmaceutical University,Shenyang,Liaoning 110016,China

Institute of Drug Research in Medicine Capital of China,Benxi,Liaoning 117000,China

Zhejiang Shapuaisi Pharmaceutical Co.,Ltd.,Pinghu,Zhejiang 314299,China

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基金：

National Natural Science Foundation of ChinaLiaoning Province Education Administration of ChinaLiaoning Provincial Foundation of Natural ScienceChina Postdoctoral Science FoundationProgram for the Innovative Research Team of the Ministry of EducationProgram for the Liaoning Innovative Research Team in University

项目编号：

22277082UKQZ20222362022-MS-2452022MD723807

出版年：

2024

DOI：

10.1002/cjoc.202300727

中国化学(英文版)

中国化学会上海有机化学研究所

中国化学(英文版)

CSTPCD

影响因子：0.848

ISSN：1001-604X

年,卷(期)：2024.42(12)