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research article

An Enantioselective Total Synthesis of (−)-Isoschizogamine

Xu, Zhengren  
•
Bao, Xu  
•
Wang, Qian  
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2015
Angewandte Chemie International Edition

A concise enantioselective total synthesis of (¢)- isoschizogamine, a complex bridged polycyclic monoterpene indole alkaloid, was accomplished. N-Alkylation of an enantio- enriched imine with an alkyl iodide afforded an iminium salt, which, upon heating by microwave irradiation in the presence of pivalic acid, was converted into the hexacyclic structure of natural product by a complex but ordered domino sequence. The one-pot process leading to the formation of one C¢C bond and three C¢N bonds created three rings and three contiguous stereogenic centers with complete control of both the relative and absolute stereochemistry.

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Type
research article
DOI
10.1002/anie.201508150
Web of Science ID

WOS:000367723400064

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

2015

Publisher

Wiley-Blackwell

Published in
Angewandte Chemie International Edition
Volume

54

Start page

14937

End page

14940

Subjects

alkaloids

•

cyclizations

•

heterocycles

•

natural products

•

total synthesis

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSPN  
Available on Infoscience
November 27, 2015
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/120832
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