Strategies for total synthesis of bispyrrolidinoindoline alkaloids
Natural Product Reports Pub Date: 2022-03-17 DOI: 10.1039/D1NP00060H
Abstract
Covering up to 2021
Complex cyclotryptamine alkaloids with a bispyrrolidino[2,3-b]indoline (BPI) skeleton are an intriguing family of natural products, exhibiting wide systematic occurrences, large structural diversity, and multiple biological activities. Based on their structural characteristics, BPI alkaloids can be classified into chimonanthine-type BPI alkaloids, BPI diketopiperazines, and BPI epipolythiodiketopiperazines. These intricate molecules have captivated great attention soon after their isolation and identification in the 1960s. Due to the structural complexity, the total synthesis of these cyclotryptamine alkaloids is challenging. Nevertheless, remarkable progress has been achieved in the last six decades; in particular, several methods have been successfully established for the construction of vicinal all-carbon quaternary stereocenters. In this review, the structural diversity and chemical synthesis of these BPI alkaloids were summarized. BPI alkaloids are mainly synthesized by the methods of oxidative dimerization, reductive dimerization, and alkylation of bisoxindole. The purpose of this review is to present overall strategies for assembling the BPI skeleton and efforts towards controlling the stereocenters.
Recommended Literature
- [1] Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements Analyst, 1991,116, 1125-1130 10.1039/AN9911601125
- [2] Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond? Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin LiuChem. Commun., 2018,54, 10092-10095 10.1039/C8CC05410J
- [3] Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings Analyst, 1996,121, 785-788 10.1039/AN9962100785
- [4] Evidence of rutile-to-anatase photo-induced electron transfer in mixed-phase TiO2 by solid-state NMR spectroscopy? Weili Dai,Guangjun Wu,Michael HungerChem. Commun., 2015,51, 13779-13782 10.1039/C5CC04971G
- [5] Evolution of shape, size, and areal density of a single plane of Si nanocrystals embedded in SiO2 matrix studied by atom probe tomography Bin Han,Yasuo Shimizu,Gabriele Seguini,Celia Castro,Gérard Ben Assayag,Koji Inoue,Yasuyoshi Nagai,Sylvie Schamm-Chardon,Michele PeregoRSC Adv., 2016,6, 3617-3622 10.1039/C5RA26710B
- [6] Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR? Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing XiaNanoscale, 2020,12, 20456-20466 10.1039/D0NR04995F
- [7] Emerging investigator series: heterogeneous reactions of sulfur dioxide on mineral dust nanoparticles: from single component to mixed components? Tao Wang,Yangyang Liu,Yue Deng,Hongbo Fu,Jianmin ChenEnviron. Sci.: Nano, 2018,5, 1821-1833 10.1039/C8EN00376A
- [8] Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries? Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde WangJ. Mater. Chem. A, 2018,6, 516-526 10.1039/C7TA08423D
- [9] Establishing plasmon contribution to chemical reactions: alkoxyamines as a thermal probe? Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. MarqueChem. Sci., 2021,12, 4154-4161 10.1039/D0SC06470J
- [10] Fc microparticles can modulate the physical extent and magnitude of complement activity? David White,Sean R. StowellBiomater. Sci., 2017,5, 463-474 10.1039/C6BM00608F
Journal Name：Natural Product Reports
research_products
-
CAS no.: 89640-58-4
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)