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.

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.

scholarly journals The chemistry of mavacurane alkaloids: a rich source of bis-indole alkaloids

2021 ◽  
Author(s):  
Audrey Mauger ◽  
Maxime Jarret ◽  
Cyrille Kouklovsky ◽  
Erwan Poupon ◽  
Laurent Evanno ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids ◽  
Rich Source ◽  
Monoterpene Indole Alkaloids

This review presents the chemistry of mavacuranes, a subfamily of the monoterpene indole alkaloids, from their isolation, biosynthesis, total synthesis to their tendency to assemble with other partners to form intricate bis-indole alkaloids.

scholarly journals Total syntheses of all tri-oxygenated 16-phytoprostane classes via a common precursor constructed by oxidative cyclization and alkyl–alkyl coupling reactions as the key steps

2017 ◽  
Vol 15 (44) ◽  
pp. 9408-9414 ◽  
Author(s):  
Jakub Smrček ◽  
Radek Pohl ◽  
Ullrich Jahn
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Common Precursor ◽  
Key Steps

A parallel total synthesis of 16-F1t-, 16-E1-phytoprostanes and a first synthesis of 16-D1t-phytoprostanes based on a common precursor are described.

scholarly journals Enantioselective Total Synthesis of Cymoside through a Bioinspired Oxidative Cyclization of a Strictosidine Derivative

2019 ◽  
Vol 132 (4) ◽  
pp. 1543-1547 ◽  
Author(s):  
Yingchao Dou ◽  
Cyrille Kouklovsky ◽  
Vincent Gandon ◽  
Guillaume Vincent
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Enantioselective Total Synthesis

scholarly journals Total synthesis of ochnaflavone

2013 ◽  
Vol 9 ◽  
pp. 1346-1351 ◽  
Author(s):  
Monica M Ndoile ◽  
Fanie R van Heerden
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Experimental Conditions ◽  
Total Syntheses ◽  
Diaryl Ether ◽  
Key Steps

The first total syntheses of ochnaflavone, an asymmetric biflavone consisting of apigenin and luteolin moieties, and the permethyl ether of 2,3,2'',3''-tetrahydroochnaflavone have been achieved. The key steps in the synthesis of ochnaflavone were the formation of a diaryl ether and ring cyclization of an ether-linked dimeric chalcone to assemble the two flavone nuclei. Optimal experimental conditions for the oxidative cyclization to form ochnaflavone were established.

Sign in / Sign up

Export Citation Format

Share Document