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research article

Enantioselective Synthesis of (+)-Peganumine A

Piemontesi, Cyril  
•
Wang, Qian  
•
Zhu, Jieping  
2016
Journal of the American Chemical Society

A gram-scale enantioselective total synthesis of (+)-peganumine A was accomplished in 7 steps from commercially available 6-methoxytryptamine. Key steps included (a) a Liebeskind−Srogl cross-coupling; (b) a one-pot construction of the tetracyclic skeleton from an ω-isocyano-γ-oxo-aldehyde via a sequence of an unprecedented C−C bond forming lactamization and a transannular condensation; (c) a one-pot organocatalytic process merging two achiral building blocks into an octacyclic structure via a sequence of enantioselective Pictet−Spengler reaction followed by a transannular cyclization. This last reaction created two spirocycles and a 2,7-diazabicyclo[2.2.1]heptan-3-one unit with excellent control of both the absolute and relative stereochemistry of the two newly created quaternary stereocenters.

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Type
research article
DOI
10.1021/jacs.6b07846
Web of Science ID

WOS:000382901800021

Author(s)
Piemontesi, Cyril  
Wang, Qian  
Zhu, Jieping  
Date Issued

2016

Publisher

American Chemical Society

Published in
Journal of the American Chemical Society
Volume

138

Issue

35

Start page

11148

End page

11151

Editorial or Peer reviewed

NON-REVIEWED

Written at

EPFL

EPFL units
LSPN  
Available on Infoscience
September 14, 2016
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/129329
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