A Divergent Enantioselective Total Synthesis of Post‐Iboga Indole Alkaloids

2020 ◽  
Vol 132 (42) ◽  
pp. 18890-18899
Author(s):  
Jie Zhou ◽  
Dong‐Xing Tan ◽  
Fu‐She Han
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids ◽  
Enantioselective Total 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.

Enantioselective total synthesis of (+)-arborescidine C and related tetracyclic indole alkaloids using organocatalysis

2017 ◽  
Vol 15 (16) ◽  
pp. 3408-3412 ◽  
Author(s):  
Vishal M. Sheth ◽  
Bor-Cherng Hong ◽  
Gene-Hsiang Lee
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids ◽  
Enantioselective Synthesis ◽  
Cyclization Reaction ◽  
Enantioselective Total Synthesis

Enantioselective synthesis of (+)-arborescidine C was achieved by the key step of Pictet–Spengler cyclization reaction with a Jacobsen-type thiourea organocatalyst.

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 Enantioselective Total Synthesis of (+)‐Garsubellin A

2021 ◽  
Author(s):  
Dongseok Jang ◽  
Minchul Choi ◽  
Jinglong Chen ◽  
Chulbom Lee
Keyword(s):  
Total Synthesis ◽  
Enantioselective Total Synthesis

Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity

2021 ◽  
Author(s):  
Robert M. Hohlman ◽  
David H. Sherman
Keyword(s):  
Biological Activity ◽  
Total Synthesis ◽  
Indole Alkaloids ◽  
Recent Advances

This review covers isolation, biological activity, an overview of total synthesis efforts and recent biosynthetic discoveries related to hapalindole-type indole alkaloids.

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.

Enantioselective Total Synthesis of ( – )‐Spiroxins A, C and D

2021 ◽  
Author(s):  
Xin Shu ◽  
Chong-Chong Chen ◽  
Tao Yu ◽  
Jiayi Yang ◽  
Xiangdong Hu
Keyword(s):  
Total Synthesis ◽  
Enantioselective Total Synthesis
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