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  4. Palladium-Catalyzed Decarboxylative Vinylation of Potassium Nitrophenyl Acetate: Application to the Total Synthesis of (±)-Goniomitine
 
research article

Palladium-Catalyzed Decarboxylative Vinylation of Potassium Nitrophenyl Acetate: Application to the Total Synthesis of (±)-Goniomitine

Xu, Zhengren  
•
Wang, Qian  
•
Zhu, Jieping  
2013
Angewandte Chemie International Edition

Merge and divert. (±)-goniomitine was synthesized featuring two key steps: a) fragment coupling to functionalized cyclopentene by a novel palladium-catalyzed decarboxylative vinylation reaction and b) an unprecedented one-pot integrated oxidation/reduction/cyclization (IORC) process to convert the substituted cyclopentene to tetracyclic skeleton of goniomitine. In this IORC process, oxidative scission of one double bond, reduction of azido and nitro groups, formation of three C-N bonds with the concurrent formation of three rings took place with high degree of chemo-, regio- and diastereo-selectivities.

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Type
research article
DOI
10.1002/anie.201209970
Web of Science ID

WOS:000316340700041

Author(s)
Xu, Zhengren  
Wang, Qian  
Zhu, Jieping  
Date Issued

2013

Publisher

Wiley-Blackwell

Published in
Angewandte Chemie International Edition
Volume

52

Issue

11

Start page

3272

End page

3276

Subjects

decarboxylative coupling

•

goniomitine

•

Indole Alkaloid

•

natural products

•

palladium

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSPN  
Available on Infoscience
March 8, 2013
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/90170
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