Total Syntheses of Zwitterionic Indole Alkaloids, Flavocarpine and Dihydrovincarpine, by Extended Method for Substituted Pyridine Synthesis through Azaelectrocyclization

Heterocycles ◽  
2015 ◽  
Vol 90 (1) ◽  
pp. 150 ◽  
Author(s):  
Toyoharu Kobayashi ◽  
Shigeo Katsumura ◽  
Yoshikatsu Hirose ◽  
Hiroshi Tsuchikawa
Keyword(s):  
Indole Alkaloids ◽  
Total Syntheses ◽  
Pyridine Synthesis

scholarly journals Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Enantioselective Total Synthesis of Mavacuran Alkaloids

2019 ◽  
Author(s):  
Maxime Jarret ◽  
Victor Turpin ◽  
Aurélien Tap ◽  
Jean-Francois Gallard ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indole Alkaloids ◽  
Oxidative Cyclization ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor ◽  
Monoterpene Indole Alkaloids ◽  
Coupling Approach

We report the enantioselective total syntheses of mavacurans alkaloids, (+)-taberdivarine H, (+)-16-hydoxymethyl-pleiocarpamine, (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterpene indole alkaloids is a target of choice since some of its members are subunits of intricate bisindole alkaloids such as bipleiophylline. Inspired by the biosynthetic hypothesis, we explored an oxidative coupling approach from the geissoschizine framework to form the N1-C16 bond. Quaternization of the aliphatic nitrogen was key to achieve the oxidative coupling induced by KHMDS/I<sub>2 </sub>since<sub> </sub>it hides the nucleophilicity of the aliphatic nitrogen and locks the required cis conformation.

Asymmetric Total Syntheses of Kopsia Indole Alkaloids

2017 ◽  
Vol 129 (13) ◽  
pp. 3757-3761 ◽  
Author(s):  
Lingying Leng ◽  
Xiaohan Zhou ◽  
Qi Liao ◽  
Falu Wang ◽  
Hao Song ◽  
...  
Keyword(s):  
Indole Alkaloids ◽  
Total Syntheses
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