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research article

Total Synthesis of (±)-Strictamine

Ren, Weiwu  
•
Wang, Qian  
•
Zhu, Jieping  
2016
Angewandte Chemie International Edition

The total synthesis of strictamine has been achieved in nine steps from a known enol triflate. Characteristic features of our approach included: a) creation of a C7 all-carbon quaternary stereocenter at an early synthetic stage; b) use of an N,N-dimethyl tertiary amine as a surrogate of the primary amine for the rapid build-up of a functionalized 2-azabicyclo-[3,3,1]nonan-9-one skeleton (achieved by using a reaction sequence of alpha-bromination of the ketone, followed by a stereo convergent intramolecular nucleophilic substitution reaction); and c) a late-stage construction of the indolenine unit.

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Type
research article
DOI
10.1002/anie.201511638
Web of Science ID

WOS:000371418200053

Author(s)
Ren, Weiwu  
Wang, Qian  
Zhu, Jieping  
Date Issued

2016

Publisher

Wiley-Blackwell

Published in
Angewandte Chemie International Edition
Volume

55

Issue

10

Start page

3500

End page

3503

Subjects

alkaloids

•

cyclizations

•

heterocycles

•

natural products

•

total synthesis

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSPN  
Available on Infoscience
February 27, 2016
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/124442
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