Symmetric Cytotoxicity Trimeric and Dimeric Indole Alkaloids from Bousigonia angustifolia

2021 ◽  
Author(s):  
Bao Bao SHi ◽  
Jing S Lu ◽  
Jing Wu ◽  
Mei F Bao ◽  
Xiang H Cai
Keyword(s):  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Ring System ◽  
System P

The first symmetric indole alkaloid trimer bousangustine A as well as dimeric ones, bousangustines B−C was isolated from trunks of Bousigonia angustifolia. The structures featuring a symmetric 6/9/5/6 ring system...

scholarly journals Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi

2018 ◽  
Vol 35 (6) ◽  
pp. 532-558 ◽  
Author(s):  
Kimberly R. Klas ◽  
Hikaru Kato ◽  
Jens C. Frisvad ◽  
Fengan Yu ◽  
Sean A. Newmister ◽  
...  
Keyword(s):  
Indole Alkaloids ◽  
Ring System ◽  
System P ◽  
Terrestrial Fungi

Various fungi of the generaAspergillus,Penicillium, andMalbrancheaproduce prenylated indole alkaloids possessing a bicyclo[2.2.2]diazaoctane ring system.

Direct N-acylation of sulfoximines with carboxylic acids catalyzed by the B3NO2 heterocycle

2017 ◽  
Vol 53 (54) ◽  
pp. 7447-7450 ◽  
Author(s):  
Hidetoshi Noda ◽  
Yasuko Asada ◽  
Masakatsu Shibasaki ◽  
Naoya Kumagai
Keyword(s):  
Carboxylic Acids ◽  
Ring System ◽  
System P

Dehydrative coupling of sulfoximines and carboxylic acids is rendered catalytic by a heterocyclic catalyst featuring the B3NO2 ring system.

Synthesis, computational, and spectroscopic analysis of tunable highly fluorescent BN-1,2-azaborine derivatives containing the N-BOH moiety

2017 ◽  
Vol 15 (48) ◽  
pp. 10172-10183 ◽  
Author(s):  
Carl Jacky Saint-Louis ◽  
Renée N. Shavnore ◽  
Caleb D. C. McClinton ◽  
Julie A. Wilson ◽  
Lacey L. Magill ◽  
...  
Keyword(s):  
Electron Donor ◽  
Spectroscopic Analysis ◽  
Ring System ◽  
Quantum Yields ◽  
System P ◽  
Donor And Acceptor ◽  
Electron Donor And Acceptor

Methods to tune the luminescence wavelength and the quantum yields by controlling the power and location of electron-donor and acceptor substituents on the ring system.

scholarly journals Trimerisation of carbon suboxide at a di-titanium centre to form a pyrone ring system

2018 ◽  
Vol 9 (22) ◽  
pp. 5008-5014 ◽  
Author(s):  
Nikolaos Tsoureas ◽  
Jennifer C. Green ◽  
F. Geoffrey N. Cloke ◽  
Horst Puschmann ◽  
S. Mark Roe ◽  
...  
Keyword(s):  
Ring System ◽  
Carbon Suboxide ◽  
Pyrone Ring ◽  
System P

Bis(pentalene)dititanium Ti2(μ:η5,η5-Pn†)2 trimerises carbon suboxide (OCCCO) to form [{Ti2(μ:η5,η5-Pn†)2}{μ-C9O6}], which contains a 4-pyrone core, via the monoadduct [Ti2(μ:η5,η5-Pn†)2 (η2-C3O2)].

Total Synthesis of (–)-Alstofolinine A: Selected Furan Oxidation/ Cyclization Cascade

Synlett ◽  
2019 ◽  
Vol 31 (01) ◽  
pp. 7-12 ◽  
Author(s):  
Ye Zhang ◽  
Lei Zhang ◽  
Xiangbing Qi
Keyword(s):  
Total Synthesis ◽  
Common Core ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Asymmetric Total Synthesis ◽  
Ring Systems ◽  
Synthetic Strategy ◽  
Nucleophilic Addition Reaction

Indole-fused tetracyclic ring systems containing nitrogen atoms are common core skeletons of many indole alkaloids such as sarpagine, macroline, and ajmaline. Efficient and stereoselective construction of these ring systems can promote the development of the corresponding alkaloid syntheses. In this article, we briefly summarize our current progress toward the application of the aza-Achmatowicz reaction and indole nucleophilic addition reaction cascade for the first asymmetric total synthesis of the macroline-type indole alkaloid (–)-Alstofolinine A. Our synthetic strategy is based on furan oxidation/rearrangement and proceeds from easily accessible materials such as indole and furan derivatives.

5-Methyltryptophan Resistant Cells of Catharanthus roseus

1979 ◽  
Vol 34 (7-8) ◽  
pp. 541-545 ◽  
Author(s):  
Jürgen Schallenberg ◽  
Jochen Berlin
Keyword(s):  
Catharanthus Roseus ◽  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Synthetase Activity ◽  
Wild Type ◽  
Free Tryptophan ◽  
Alkaloid Synthesis ◽  
Resistant Cells

Several cell lines resistant to 5-methyltryptophan were selected from wild type cells of different Catharanthus roseus suspension cultures. The resistant cells had up to 30 times tne normal levels of free tryptophan. Despite the increased pool size of tryptophan anthranilate synthetase activity of resistant cells was as sensitive to inhibition by ʟ-tryptophan as wild type cells. The overproduction of tryptophan did not lead to intensified accumulation of tryptamine nor of indole alkaloids. This was supported by a low conversion of tryptophan to tryptamine in vivo and in vitro. The overpro­duction of one of the primary precursors was evidently not sufficient to stimulate the rate of indole alkaloid synthesis in Catharanthus cells.

Photocyclization of aryl enaminones. An efficient route to indole alkaloid synthons

1989 ◽  
Vol 67 (2) ◽  
pp. 213-219 ◽  
Author(s):  
Daniel Gardette ◽  
Jean-Claude Gramain ◽  
Marie-Eve Lepage ◽  
Yves Troin
Keyword(s):  
Steric Hindrance ◽  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Aromatic Substituent ◽  
Aromatic Moiety ◽  
Efficient Route

The photocyclization of enaminones was extended to aryl enaminones bearing a substituent on the aromatic moiety. This reaction was studied in order to achieve the synthesis of indole alkaloid synthons. Trials of regioselectivity control were made by using groups with enhanced steric hindrance. The reactivity of secondary enaminones was tested, and the ratio of C-alkylation to N-alkylation was shown to be dependent on the nature of the aromatic substituent. During this work, new hexahydrocarbazolones were synthesized, with substituents on the A ring or the modified C ring. Keywords: photocyclization, aryl enaminones, indole alkaloids, hexahydrocarbazolones-4, cyclopenta[b]indoles.

scholarly journals Fungal Origins of the Bicyclo[2.2.2]diazaoctane Ring System of Prenylated Indole Alkaloids

2012 ◽  
Vol 75 (4) ◽  
pp. 812-833 ◽  
Author(s):  
Jennifer M. Finefield ◽  
Jens C. Frisvad ◽  
David H. Sherman ◽  
Robert M. Williams
Keyword(s):  
Indole Alkaloids ◽  
Ring System
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