Stereoselective Total Synthesis of (+)-Nephrosteranic Acid and (+)-Roccellaric Acid through Asymmetric Dihydroxylation and Johnson-Claisen Rearrangement
DSpace at IIT Bombay
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Title |
Stereoselective Total Synthesis of (+)-Nephrosteranic Acid and (+)-Roccellaric Acid through Asymmetric Dihydroxylation and Johnson-Claisen Rearrangement
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Creator |
FERNANDES, RA
CHOWDHURY, AK |
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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 |
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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.
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Publisher |
WILEY-BLACKWELL
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Date |
2012-06-26T04:48:58Z
2012-06-26T04:48:58Z 2011 |
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Type |
Article
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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 |
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Language |
English
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