Ten-Step Total Synthesis of (-)-Andranginine

被引：1

作者：

Zhao, Yulong ^{[1
]}

Li, Jiaxin ^{[1
]}

Ma, Ruize ^{[1
]}

He, Feifei ^{[1
]}

Shi, Hongliang ^{[1
]}

Duan, Xiaoguang ^{[1
]}

Li, Huilin ^{[1
]}

Xie, Xingang ^{[1
]}

She, Xuegong ^{[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 | 2022年 / 24卷 / 37期

基金：

美国国家科学基金会;

关键词：

INDOLE ALKALOIDS; ASYMMETRIC-SYNTHESIS; ANDRANGININE; MELODINUS;

D O I：

10.1021/acs.orglett.2c02927

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the indole alkaloid (-)-an-dranginine has been achieved in 10 steps. Key reactions of the synthesis include a nucleophilic addition of acetylenyl anion to chiral N-sulfinyl imine, an intramolecular N-alkylation reaction to close the C ring, and a dienyne metathesis cascade reaction to construct the DE rings. Meanwhile, 16-epi-(-)-andranginine was also obtained with the developed strategy.

引用

页码：6880 / 6883

页数：4

共 50 条

[1] A Ten-Step Total Synthesis of SperadineC
Liu, Haichao
Chen, Lijun
Yuan, Kuo
Jia, Yanxing
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (19) : 6362 - 6365
[2] Ten-Step Asymmetric Total Synthesis of (+)-Pepluanol A
Yuan, Po
Gerlinger, Christa K. G.
Herberger, Jan
Gaich, Tanja
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (31) : 11934 - 11938
[3] Ten-step enantioselective total synthesis of the akuammiline alkaloid vincorine
Horning, Benjamin D.
MacMillan, D. W. C.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
[4] Ten-Step Total Synthesis of (±)-Phaeocaulisin A Enabled by Cyclopropanol Ring-Opening Carbonylation
Liu, Chang
Zhang, Mingyu
Zeng, Lidan
Wan, Yong
Dai, Mingji
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (47) : 32276 - 32282
[5] A Ten-Step Process for Energy Analysis
Stowe, Michael L.
CHEMICAL ENGINEERING PROGRESS, 2018, 114 (11) : 36 - 41
[6] Ten-step asymmetric total syntheses of potent antibiotics anthracimycin and anthracimycin B
Tian, Peilin
Ye, Wenkang
Zhang, Xiayan
Tong, Yi
Qian, Pei-Yuan
Tong, Rongbiao
Chemical Science, 2022, 40
[7] Ten-step asymmetric total syntheses of potent antibiotics anthracimycin and anthracimycin B
Tian, Peilin
Ye, Wenkang
Zhang, Xiayan
Tong, Yi
Qian, Pei-Yuan
Tong, Rongbiao
CHEMICAL SCIENCE, 2022, 13 (43) : 12776 - 12781
[8] GE's ten-step talent plan
Charan, R
FORTUNE, 2000, 141 (08) : 232 - 232
[9] Ten-step mechanism for the pitting corrosion of aluminium
Reboul, M.C.
Warner, T.J.
Mayet, H.
Baroux, B.
Materials Science Forum, 1996, 217-222 (pt 3) : 1553 - 1558
[10] A ten-step mechanism for the pitting corrosion of aluminium
Reboul, MC
Warner, TJ
Mayet, H
Baroux, B
ALUMINIUM ALLOYS: THEIR PHYSICAL AND MECHANICAL PROPERTIES, PTS 1-3, 1996, 217 : 1553 - 1558

← 1 2 3 4 5 →