A pair of new oxindole alkaloids isolated from Uncaria macrophylla

2021 ◽  
pp. 1-7
Author(s):  
Xin-Xin Liang ◽  
Jin-Xuan Yang ◽  
Jian-Mei Li ◽  
Jia-Bi Huang ◽  
Liu-Meng Yang ◽  
...  
Keyword(s):  
Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 428
Author(s):  
Nihan Yayik ◽  
Maria Pérez ◽  
Elies Molins ◽  
Joan Bosch ◽  
Mercedes Amat

A synthetic route for the enantioselective construction of the tetracyclic spiro[indolizidine-1,3′-oxindole] framework present in a large number of oxindole alkaloids, with a cis H-3/H-15 stereochemistry, a functionalized two-carbon substituent at C-15, and an E-ethylidene substituent at C-20, is reported. The key steps of the synthesis are the generation of the tetracyclic spirooxindole ring system by stereoselective spirocyclization from a tryptophanol-derived oxazolopiperidone lactam, the removal of the hydroxymethyl group, and the stereoselective introduction of the E-ethylidene substituent by acetylation at the α-position of the lactam carbonyl, followed by hydride reduction and elimination. Following this route, the 21-oxo derivative of the enantiomer of the alkaloid 7(S)-geissoschizol oxindole has been prepared.


2010 ◽  
Vol 48 (6) ◽  
pp. 716-721 ◽  
Author(s):  
Ijaz Ahmad ◽  
Fozia Ijaz ◽  
Itrat Fatima ◽  
Nisar Ahmad ◽  
Shilin Chen ◽  
...  

ChemInform ◽  
2015 ◽  
Vol 46 (10) ◽  
pp. no-no
Author(s):  
Xiao Hu ◽  
Qi-Wen Xia ◽  
Yang-Yang Zhao ◽  
Qiu-Hong Zheng ◽  
Qin-Ying Liu ◽  
...  

1994 ◽  
Vol 35 (17) ◽  
pp. 2651-2654 ◽  
Author(s):  
Andrew C. Peterson ◽  
James M. Cook

2020 ◽  
Vol 83 (7) ◽  
pp. 2165-2177
Author(s):  
Laura Flores-Bocanegra ◽  
Huzefa A. Raja ◽  
Tyler N. Graf ◽  
Mario Augustinović ◽  
E. Diane Wallace ◽  
...  

2011 ◽  
Vol 74 (1) ◽  
pp. 12-15 ◽  
Author(s):  
Kou Wang ◽  
Xiao-Yu Zhou ◽  
Yuan-Yuan Wang ◽  
Ming-Ming Li ◽  
Yin-Shan Li ◽  
...  
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