Recent advances in the total synthesis of monoterpenoid indole alkaloids enabled by asymmetric catalysis

被引:31
作者
Liu, Xiao-Yu
Qin, Yong [1 ]
机构
[1] Sichuan Univ, Sichuan Engn Lab Plant Sourced Drug, West China Sch Pharm, Key Lab Drug Targeting & Drug Delivery Syst,Educ M, Chengdu 610041, Peoples R China
来源
GREEN SYNTHESIS AND CATALYSIS | 2022年 / 3卷 / 01期
基金
中国国家自然科学基金;
关键词
Asymmetric catalysis; Total synthesis; Indole alkaloid; Natural product; Enantioselectivity; PICTET-SPENGLER REACTIONS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ASPIDOSPERMA ALKALOIDS; EFFICIENT SYNTHESIS; MICHAEL ADDITION; ALKYLATION; STRATEGY; ACIDS; CONSTRUCTION; ALDEHYDES;
D O I
10.1016/j.gresc.2021.10.009
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric catalysis has continued to enable the preparation of optically active natural products over the past decade. This minireview summarizes progress in the catalytic enantioselective total synthesis of complex mon-oterpenoid indole alkaloids covering the reports from 2019 to June 2021. In particular, the generation of the key chiral stereogenic centers with metal catalysts and organocatalysts has been highlighted, showcasing the power of asymmetric catalysis protocols in accessing complex molecular architectures.
引用
收藏
页码:25 / 39
页数:15
相关论文
共 74 条
[1]  
Adams Gregory L, 2016, Alkaloids Chem Biol, V76, P171, DOI 10.1016/bs.alkal.2015.08.001
[2]   Asymmetric Total Synthesis of (-)-Arborisidine and (-)-19-epi-Arborisidine Enabled by a Catalytic Enantioselective Pictet-Spengler Reaction [J].
Andres, Remi ;
Wang, Qian ;
Zhu, Jieping .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (33) :14276-14285
[3]   Scalable Enantioselective Total Synthesis of (-)-Goniomitine [J].
Bin, Huai-Yu ;
Wang, Ke ;
Yang, Dan ;
Yang, Xiao-Hui ;
Xie, Jian-Hua ;
Zhou, Qi-Lin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (04) :1174-1177
[4]   FUNCTIONALIZED 2-AZABICYCLO[3.3.1]NONANES .6. STUDIES DIRECTED TO THE SYNTHESIS OF PENTACYCLIC STRYCHNOS INDOLE ALKALOIDS [J].
BONJOCH, J ;
CASAMITJANA, N ;
QUIRANTE, J ;
RODRIGUEZ, M ;
BOSCH, J .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :267-275
[5]   Highly Enantioselective Pictet-Spengler Reactions with α-Ketoamide-Derived Ketimines: Access to an Unusual Class of Quaternary α-Amino Amides [J].
Bou-Hamdan, Farhan R. ;
Leighton, James L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (13) :2403-2406
[6]   Enantioselective total synthesis of clavirolide C. applications of Cu-catalyzed asymmetric conjugate additions and Ru-catalyzed ring-closing metathesis [J].
Brown, M. Kevin ;
Hoveyda, Amir H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (39) :12904-+
[7]   METHODS FOR INDOLE ALKALOID SYNTHESIS - A STUDY OF THE COMPATIBILITY OF THE INDOLE 2,3-QUINODIMETHANE STRATEGY FOR THE SYNTHESIS OF 16-METHOXY-SUBSTITUTED ASPIDOSPERMA-TYPE ALKALOIDS - SYNTHESIS OF (+)- AND (-)-16-METHOXYTABERSONINE [J].
CARDWELL, K ;
HEWITT, B ;
LADLOW, M ;
MAGNUS, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2242-2248
[8]   Parallel kinetic resolution of racemic mixtures: a new strategy for the preparation of enantiopure compounds? [J].
Dehli, JR ;
Gotor, V .
CHEMICAL SOCIETY REVIEWS, 2002, 31 (06) :365-370
[9]   TiCl3-Mediated Synthesis of 2,3,3-Trisubstituted Indolenines: Total Synthesis of (+)-1,2-Dehydroaspidospermidine, (+)-Condyfoline, and (-)-Tubifoline [J].
Delayre, Bastien ;
Piemontesi, Cyril ;
Wang, Qian ;
Zhu, Jieping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (33) :13990-13997
[10]   Synthesis of Cyclic Enones via Direct Palladium-Catalyzed Aerobic Dehydrogenation of Ketones [J].
Diao, Tianning ;
Stahl, Shannon S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (37) :14566-14569