Concise total synthesis of (±)-aspidospermidine via an oxidative Hosomi-Sakurai process

被引：70

作者：

Sabot, Cyrille ^{[1
]}

Guerard, Kimiaka C. ^{[1
]}

Canesi, Sylvain ^{[1
]}

机构：

[1] Univ Quebec, Lab Methodol & Synth Prod Nat, Montreal, PQ H3C 3P8, Canada

来源：

CHEMICAL COMMUNICATIONS | 2009年 / 20期

基金：

加拿大自然科学与工程研究理事会;

关键词：

FORMAL 2+3 CYCLOADDITION; HYPERVALENT IODINE(III) REAGENT; BIARYL COUPLING REACTION; ASPIDOSPERMA ALKALOIDS; INDOLE ALKALOIDS; ENANTIOSPECIFIC SYNTHESIS; SUBSTITUTED PHENOLS; TRICYCLIC AMINES; RECENT PROGRESS; DERIVATIVES;

D O I：

10.1039/b903530c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise total synthesis of (+/-)-aspidospermidine has been achieved in twelve steps from inexpensive 4-ethylphenol, based on an oxidative Hosomi-Sakurai reaction via the concept of "aromatic ring umpolung".

引用

页码：2941 / 2943

页数：3

共 50 条

[31] Concise asymmetric total synthesis of lycopodine and flabelliformine via cascade cyclization reaction
Wada, Kentaro
Kogure, Noriyuki
Kitajima, Mariko
Takayama, Hiromitsu
TETRAHEDRON LETTERS, 2019, 60 (02) : 187 - 190
[32] A concise and straightforward approach to total synthesis of (+)-Strictifolione and formal synthesis of Cryptofolione via a unified strategy
Li, Xiaotong
Wang, Gaopeng
Zhang, Zhibin
Wu, Na
Yang, Qianqian
Huang, Shuangping
Wang, Xiaoji
SYNTHETIC COMMUNICATIONS, 2019, 49 (08) : 1031 - 1039
[33] Synthesis of Lactones via Electrochemical Sequential Oxidative Process
Fang, Ming
Shang, Peinan
Huang, Hai
Sun, Jianwei
Han, Zhengyu
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (34)
[34] Total synthesis of Alliacol A via oxidative cyclization reactions.
Mihelcic, JM
Moeller, KD
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U350 - U350
[35] A concise stereoselective formal total synthesis of the cytotoxic macrolide (+)-Neopeltolide via Prins cyclization
Yadav, Jhillu Singh
Kumar, Gunda Gopala Krishana Satya Narayana
TETRAHEDRON, 2010, 66 (02) : 480 - 487
[36] A Concise Total Synthesis of Steroid Scaffolds via a Palladium-Catalyzed Dearomatization Cyclization
Huang, Zhangwei
Pan, Xianhua
Guo, Lei
Tang, Wenjun
SYNLETT, 2022, 33 (17) : 1770 - 1774
[37] Cyclopentane construction via β-lactone intermediates:: Application to a concise total synthesis of (+)-brefeldin A.
Wang, YC
Romo, D
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U180 - U180
[38] Concise Total Synthesis of (±)-Pseudotabersonine via Double Ring-Closing Metathesis Strategy
Cheng, Bo
Sunderhaus, James D.
Martin, Stephen F.
ORGANIC LETTERS, 2010, 12 (16) : 3622 - 3625
[39] Concise Total Synthesis of (±)-cis-Trikentrin A and (±)-Herbindole A via Intermolecular Indole Aryne Cycloaddition
Buszek, Keith R.
Brown, Neil
Luo, Diheng
ORGANIC LETTERS, 2009, 11 (01) : 201 - 204
[40] Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction
Chen, Yuye
Chen, Wenqing
Zhang, Zhiting
Xu, Jing
CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (11) : 1267 - 1274

← 1 2 3 4 5 →