Intramolecular Dearomative Oxidative Coupling of Indoles: A Unified Strategy for the Total Synthesis of Indoline Alkaloids

2015 ◽  
Vol 48 (3) ◽  
pp. 702-711 ◽  
Author(s):  
Weiwei Zi ◽  
Zhiwei Zuo ◽  
Dawei Ma
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indoline Alkaloids

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.

Eight‐Step Total Synthesis of Phalarine by Bioinspired Oxidative Coupling of Indole and Phenol

2019 ◽  
Vol 131 (18) ◽  
pp. 6135-6139 ◽  
Author(s):  
Lei Li ◽  
Kuo Yuan ◽  
Qianlan Jia ◽  
Yanxing Jia
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling

scholarly journals Total Synthesis of Phyllanemblinin B

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1389-1393
Author(s):  
Shinnosuke Wakamori ◽  
Shintaro Matsumoto ◽  
Kentaro Nishii ◽  
Takashi Tanaka ◽  
Hidetoshi Yamada
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Open Chain

A total synthesis was developed of phyllanemblinin B, a natural ellagitannin containing 1-O-galloyl and 2,4-O-hexahydroxydiphenoyl groups on a d-glucose scaffold. The use of a μ-hydroxo copper(II) complex resulted in a completely stereoselective oxidative coupling of the galloyl groups on the open-chain glucose moiety and facilitated the first total synthesis of phyllanemblinin B.

Eight‐Step Total Synthesis of Phalarine by Bioinspired Oxidative Coupling of Indole and Phenol

2019 ◽  
Vol 58 (18) ◽  
pp. 6074-6078 ◽  
Author(s):  
Lei Li ◽  
Kuo Yuan ◽  
Qianlan Jia ◽  
Yanxing Jia
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling

Total Synthesis of the Marine Metabolite (±)-Polysiphenol via Highly Regioselective Intramolecular Oxidative Coupling

2011 ◽  
Vol 74 (9) ◽  
pp. 1980-1984 ◽  
Author(s):  
Tim N. Barrett ◽  
D. Christopher Braddock ◽  
Anna Monta ◽  
Michael R. Webb ◽  
Andrew J. P. White
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling

Total Synthesis of Indoline Alkaloids: A Cyclopropanation Strategy

2011 ◽  
Vol 44 (6) ◽  
pp. 447-457 ◽  
Author(s):  
Dan Zhang ◽  
Hao Song ◽  
Yong Qin
Keyword(s):  
Total Synthesis ◽  
Indoline Alkaloids

scholarly journals Total Synthesis of Bisbibenzyl Dibenzofuran Asterelin A via Intramolecular Oxidative Coupling

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Kosho Makino ◽  
Kenichi Harada ◽  
Miwa Kubo ◽  
Hideaki Hioki ◽  
Yoshiyasu Fukuyama
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Macrocyclic Ring

Total synthesis of asterelin A was accomplished by applying intramolecular Suzuki-Miyaura and oxidative couplings to the formation of an 18-membered macrocyclic ring and a dibenzofuran respectively.

scholarly journals Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps

2018 ◽  
Vol 16 (5) ◽  
pp. 750-755 ◽  
Author(s):  
Pratap R. Jagtap ◽  
Ivana Císařová ◽  
Ullrich Jahn
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Nucleophilic Addition ◽  
Key Steps ◽  
Redox Isomerization

Three steps suffice to complete a bioinspired total synthesis of tetrahydrofuran lignans using tandem addition/isomerization/dimerization and cycloetherification reactions.

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