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  4. Enzymatic desymmetrization of 1,1 '-methylenedi-[(1R,1 ' S,3R,3 ' S,5S,5 ' R)-3-hydroxy-8-oxabicyclo[3.2.1]-oct-6-ene-1-yl]: Novel precursors of long chain polyketides
 
research article

Enzymatic desymmetrization of 1,1 '-methylenedi-[(1R,1 ' S,3R,3 ' S,5S,5 ' R)-3-hydroxy-8-oxabicyclo[3.2.1]-oct-6-ene-1-yl]: Novel precursors of long chain polyketides

Coste, G  
•
Gerber-Lemaire, S  
2005
Tetrahedron: Asymmetry

meso-1,1'-Methylenedi[(1R,1'S,3R,3'S,5S,5'R)-3-hydroxy-S-oxabicyclo[3.2. 1]oct-6-ene-1-yl] 14 obtained through the [4+3]-cycloaddition of 2,T-methylenedifuran to oxyallyl cation, followed by reduction, has been desymmetrized by means of a lipase catalyzed transesterification to afford (1 S,3S,5S)-1-[(1 R,3R,5R)-3-hydroxy-8-oxabicyclo[3.2. 1]oct-6-en-yl]methyl)-8-oxabicyclo[3.2.1]loct-6-en-3-yl acetate (-)-15 (89% ee). This compound was transformed into aromatic ester derivatives for establishing the absolute configuration. (c) 2005 Elsevier Ltd. All rights reserved.

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Type
research article
DOI
10.1016/j.tetasy.2005.05.038
Web of Science ID

WOS:000230879800013

Author(s)
Coste, G  
Gerber-Lemaire, S  
Date Issued

2005

Published in
Tetrahedron: Asymmetry
Volume

16

Issue

13

Start page

2277

End page

2283

Subjects

diels-alder addition

•

polyene macrolide antibiotics

•

asymmetric-synthesis

•

enantioselective synthesis

•

stereoselective-synthesis

•

synthetic correlation

•

aldol reactions

•

methyl ketones

•

amphotericin-b

•

filipin-iii

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LGSA  
Available on Infoscience
November 9, 2005
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/219456
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