Asymmetric total syntheses of five pyrrole-type Stemona alkaloids?
Organic Chemistry Frontiers Pub Date: 2022-05-23 DOI: 10.1039/D2QO00456A
Abstract
The asymmetric total syntheses of five pyrrole-type Stemona alkaloids and two stereoisomers were accomplished, among which 3-n-butylneostemonine and bisdehydroneostemonine were synthesized for the first time, and the NMR data of bisdehydroneostemonine were revised. Specifically, the 5/7 skeleton of stemoamide was established by employing Prins cyclization, and didehydrostemoamide was obtained from stemoamide using our method of Lawesson's reagent promoted pyrrole synthesis. Using didehydrostemoamide as the common intermediate, five pyrrole Stemona alkaloids were divergently synthesized. This research has enriched the transformation pattern of Stemona alkaloids.
Recommended Literature
- [1] An approach for correlating the structural and electrical properties of Zr4+-modified SrBi4Ti4O15/SBT ceramic Priyambada Nayak,Tanmaya Badapanda,Anil Kumar Singh,Simanchalo PanigrahiRSC Adv., 2017,7, 16319-16331 10.1039/C7RA00366H
- [2] Alumina coating on 5 V lithium cobalt fluorophosphate cathode material for lithium secondary batteries – synthesis and electrochemical properties? S. Amaresh,K. Karthikeyan,K. J. Kim,Y. S. LeeRSC Adv., 2014,4, 23107-23115 10.1039/C4RA02318H
- [3] Alternative mixtures to R-600a. Theoretical assessment and experimental energy evaluation of binary mixtures in a commercial cooler: Mélanges alternatifs au R-600a. évaluation théorique et évaluation énergétique expérimentale de mélanges binaires dans un refroidisseur commercial. DanielCalleja-Anta,DanielSánchez,LauraNebot-Andres,RamónCabello,RodrigoLlopis 10.1016/j.ijrefrig.2023.05.009
- [4] An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis? Supaporn Sawadjoon,Joseph S. M. SamecOrg. Biomol. Chem., 2011,9, 2548-2554 10.1039/C0OB00383B
- [5] An Aptamer Bio-barCode (ABC) assay using SPR, RNase H, and probes with RNA and gold-nanorods for anti-cancer drug screening Chengbin Yang,Hing Lun Tsang,Pui Man Lau,Ken-Tye Yong,Ho Pui Ho,Siu Kai KongAnalyst, 2017,142, 3579-3587 10.1039/C7AN01026E
- [6] An insight into the hybridization mechanism of hairpin DNA physically immobilized on chemically modified graphenes Adeline Huiling Loo,Alessandra Bonanni,Martin PumeraAnalyst, 2013,138, 467-471 10.1039/C2AN36199J
- [7] An amorphous Cu–In–S nanoparticle-based precursor ink with improved atom economy for CuInSe2 solar cells with 10.85% efficiency? Green Chem., 2017,19, 1268-1277 10.1039/C6GC03280J
- [8] An atlas of endohedral Sc2S cluster fullerenes? Li-Hua Gan,Rui Wu,Jian-Lei Tian,Patrick W. FowlerPhys. Chem. Chem. Phys., 2017,19, 419-425 10.1039/C6CP07370K
- [9] An all-solid-state asymmetric device based on a polyaniline hydrogel for a high energy flexible supercapacitor? Hamid Heydari,Mohammad B. GholivandNew J. Chem., 2017,41, 237-244 10.1039/C6NJ02266A
- [10] An amide probe as a selective Al3+ and Fe3+ sensor inside the HeLa and a549 cell lines: Pictet–Spengler reaction for the rapid detection of tryptophan amino acid? Bidyut Kumar Kundu,Rinky Singh,Ritudhwaj Tiwari,Debasis NayakNew J. Chem., 2019,43, 4867-4877 10.1039/C9NJ00138G
Journal Name：Organic Chemistry Frontiers
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.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)