Record Details

Late-Stage beta-Epimerization. A Stereodivergent to Stereoconvergent Relay to the First Total Synthesis of (+)-Murolic Acid

DSpace at IIT Bombay

View Archive Info
 
 
Field Value
 
Title Late-Stage beta-Epimerization. A Stereodivergent to Stereoconvergent Relay to the First Total Synthesis of (+)-Murolic Acid
 
Creator FERNANDES, RA
PATIL, PH
CHOWDHURY, AK
 
Subject Total synthesis
Natural products
Asymmetric synthesis
Rearrangement
Epimerization
CLAISEN REARRANGEMENT
ASYMMETRIC DIHYDROXYLATION
GAMMA-BUTYROLACTONES
PARACONIC ACIDS
DRIVING FORCE
CENTRAL-ASIA
LICHEN
CARBOXYLATION
GLYCOLIPIDS
CHELATION
 
Description The first total synthesis of (+)-murolic acid is accomplished in 17 steps from ester 9 in 14.8% overall yield. The key steps involve asymmetric dihydroxylation, orthoester Johnson-Claisen rearrangement and -methylenation using Stiles reagent. A beneficial late stage -epimerization reverted a stereodivergent relay to a stereoconvergent completion of an efficient synthesis of (+)-murolic acid.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-12-28T11:17:54Z
2014-12-28T11:17:54Z
2014
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014(1)237-243
1434-193X
1099-0690
http://dx.doi.org/10.1002/ejoc.201301287
http://dspace.library.iitb.ac.in/jspui/handle/100/16338
 
Language English