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research article
An Enantioselective Total Synthesis of (−)-Isoschizogamine
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.
Type
research article
Web of Science ID
WOS:000367723400064
Author(s)
Date Issued
2015
Publisher
Published in
Volume
54
Start page
14937
End page
14940
Peer reviewed
REVIEWED
Written at
EPFL
EPFL units
Available on Infoscience
November 27, 2015
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