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  4. Phosphoric Acid Catalyzed Desymmetrization of Bicyclic Bislactones Bearing an All-Carbon Stereogenic Center: Total Syntheses of (−)-Rhazinilam and (−)-Leucomidine B
 
research article

Phosphoric Acid Catalyzed Desymmetrization of Bicyclic Bislactones Bearing an All-Carbon Stereogenic Center: Total Syntheses of (−)-Rhazinilam and (−)-Leucomidine B

Gualtierotti, Jean-Baptiste  
•
Pasche, Delphine
•
Wang, Qian  
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2014
Angewandte Chemie International Edition

In the presence of a catalytic amount of an imidodiphosphoric acid, enantioselective desymmetrization of bicyclic bislactones by reaction with alcohols took place smoothly to afford enantiomerically enriched mono acids having an all-carbon stereogenic center. Concise catalytic enantioselective syntheses of both (-)-rhazinilam and (-)-leucomidine B were subsequently developed using (S)-methyl 4-ethyl-4-formylpimelate monoacid as a common starting material.

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Type
research article
DOI
10.1002/anie.201405842
Web of Science ID

WOS:000342678200044

Author(s)
Gualtierotti, Jean-Baptiste  
Pasche, Delphine
Wang, Qian  
Zhu, Jieping  
Date Issued

2014

Publisher

Wiley-Blackwell

Published in
Angewandte Chemie International Edition
Volume

53

Issue

37

Start page

9926

End page

9930

Subjects

alkaloids

•

natural products

•

organocatalysis

•

synthetic methods

•

total synthesis

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSPN  
Available on Infoscience
September 4, 2014
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/106705
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