Enantioselective Organocatalytic Construction of Hexahydropyrroloindole by Means of -Alkylation of Aldehydes Leading to the Total Synthesis of (+)-Gliocladin C

被引：123

作者：

Song, Jin ^{[1
,2
]}

Guo, Chang ^{[1
,2
]}

Adele, Arafate ^{[1
,2
]}

Yin, Hao ^{[1
,2
]}

Gong, Liu-Zhu ^{[1
,2
]}

机构：

[1] Univ Sci & Technol China, Microscale Joint Lab Green Synthet Chem, Hefei Natl Lab Phys Sci, Hefei 230026, Peoples R China

[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 10期

关键词：

alkaloids; amines; asymmetric catalysis; phosphoric acid; total synthesis; CONCISE TOTAL-SYNTHESIS; STEREOSELECTIVE ALPHA-ALKYLATION; ALPHA; BETA-UNSATURATED KETONES; CYCLOTRYPTAMINE ALKALOIDS; MICHAEL ADDITION; GENERAL-APPROACH; PHOSPHORIC-ACID; CATALYSIS; DERIVATIVES; EFFICIENT;

D O I：

10.1002/chem.201204522

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

12-Step program: The combined use of cinchona alkaloid based amine and chiral phosphoric acid enabled the asymmetric alkylation reaction of 3-hydroxyoxindoles with aldehydes to give 3,3′-disubstituted oxindoles in excellent enantioselectivities, which allows for the enantioselective total synthesis of (+)-gliocladin C in 12 steps from 3-hydroxyoxindole with 19 % overall yield (see scheme; PMB=para-methoxybenzyl). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3319 / 3323

页数：5

共 50 条

[21] Organocatalytic Enantioselective Aziridination of α-Substituted α,β-Unsaturated Aldehydes: Asymmetric Synthesis of Terminal Aziridines
Deiana, Luca
Zhao, Gui-Ling
Lin, Shuangzheng
Dziedzic, Pawel
Zhang, Qiong
Leijonmarck, Hans
Cordova, Armando
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3201 - 3207
[22] Enantioselective Total Synthesis of [3]-Ladderanol through Late-Stage Organocatalytic Desymmetrization
Ray, Sayan
Mondal, Subhajit
Mukherjee, Santanu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (24)
[23] Racemic and enantioselective total synthesis of heliespirones A & C
Chong Huang
WenHan Zhang
Bo Liu
Science China Chemistry, 2011, 54 : 43 - 55
[24] Organocatalytic Enantioselective Friedel-Crafts Alkylation of 4,7-Dihydroindoles with α,β-Unsaturated Aldehydes: An Easy Access to 2-Substituted Indoles
Hong, Liang
Liu, Chunxia
Sun, Wangsheng
Wang, Lei
Wong, Kwokyin
Wang, Rui
ORGANIC LETTERS, 2009, 11 (10) : 2177 - 2180
[25] Organocatalytic Enantioselective Pictet-Spengler Reaction of α-Ketoesters: Development and Application to the Total Synthesis of (+)-Alstratine A
Andres, Remi
Sun, Fenggang
Wang, Qian
Zhu, Jieping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (01)
[26] Organocatalytic Enantioselective Alkylation of Pyrazol-3-ones with Isatin-Derived Ketimines: Stereocontrolled Construction of Vicinal Tetrasubstituted Stereocenters
Amr, Fares Ibrahim
Vila, Carlos
Blay, Gonzalo
Munoz, M. Carmen
Pedro, Jose R.
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (10) : 1583 - 1588
[27] Studies towards an Enantioselective Total Synthesis of Sarain A: A Concise Asymmetric Construction of the Diazatricyclic Core
Yang, Rui-Feng
Huang, Pei-Qiang
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (34) : 10319 - 10322
[28] Racemic and enantioselective total synthesis of heliespirones A&C
HUANG Chong 1
College of Chemistry
Shanghai Institute of Organic Chemistry
Science China(Chemistry), 2011, (01) : 43 - 55
[29] Enantioselective -Alkylation of Aldehydes through an Organocatalyzed C-C Bond-Scission Reaction
Huang, Huicai
Abbaraju, Santhi
Zhao, John C-G.
SYNLETT, 2016, 27 (09) : 1379 - 1382
[30] Enantioselective Catalytic Aldehyde α-Alkylation/Semipinacol Rearrangement: Construction of α-Quaternary-δ-Carbonyl Cycloketones and Total Synthesis of (+)-Cerapicol
Yang, Jie
Zhang, Xiao-Ming
Zhang, Fu-Min
Wang, Shao-Hua
Tu, Yong-Qiang
Li, Zhen
Wang, Xi-Chao
Wang, Hong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (22) : 8471 - 8475

← 1 2 3 4 5 →