Record Details

Stereoselective Total Synthesis of (+)-Nephrosteranic Acid and (+)-Roccellaric Acid through Asymmetric Dihydroxylation and Johnson-Claisen Rearrangement

DSpace at IIT Bombay

View Archive Info
 
 
Field Value
 
Title Stereoselective Total Synthesis of (+)-Nephrosteranic Acid and (+)-Roccellaric Acid through Asymmetric Dihydroxylation and Johnson-Claisen Rearrangement
 
Creator FERNANDES, RA
CHOWDHURY, AK
 
Subject BUTYROLACTONE NATURAL-PRODUCTS
CHIRAL BUTENOLIDE SYNTHONS
ENANTIOSELECTIVE SYNTHESIS
(+)-TRANS-WHISKEY LACTONE
(+)-TRANS-COGNAC LACTONE
(-)-ROCCELLARIC ACID
PARACONIC ACIDS
(-)-NEPHROSTERANIC ACID
NEPHROSTERANIC ACID
DERIVATIVES
Diastereoselectivity
Asymmetric synthesis
Dihydroxylation
Rearrangement
Total synthesis
 
Description An efficient stereoselective total synthesis of (+)-nephrosteranic acid and (+)-roccellaric acid is presented. The synthetic strategy features the regioselective asymmetric dihydroxylation of the gamma,delta-olefinic bond of a alpha,beta,gamma,delta-unsaturated ester and the Johnson-Claisen rearrangement as the key steps. The synthesis is achieved in 10 steps and 6.8% (nephrosteranic acid) and 7.6% (roccellaric acid) overall yield.
 
Publisher WILEY-BLACKWELL
 
Date 2012-06-26T04:48:58Z
2012-06-26T04:48:58Z
2011
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,(6)1106-1112
1434-193X
http://dx.doi.org/10.1002/ejoc.201001419
http://dspace.library.iitb.ac.in/jspui/handle/100/13903
 
Language English