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Synthesis of pterocarpans by means of a "Disfavored" 5-endo-trig radical cyclization reaction
Kalpathy Chidambareswaran Santhosh, Kalapattukuppuswamy Kuppuswamy B. Balasubramanian
Published in
2001
   
Issue: 18
Pages: 3461 - 3466
Abstract
A successful synthesis of pterocarpans 1, based on a "disfavored" 5-endo-trig radical cyclization reaction, has been accomplished. The radical precursor 4-(2′-bromoaryloxy)-2H-chromene 8 was synthesized in six steps, starting from aryl propynyl ether 2. On treatment with tributyltin hydride in refluxing benzene, aryl enol ether 8 underwent radical cyclization to furnish the pterocarpan 1. A deuterium label study was performed to prove the occurrence of 5-endo-trig radical cyclization. This methodology was extended further to synthesize a class of hitherto unknown pterocarpans 13. A novel and stereoselective route towards the synthesis of aryl ethers of bromohydrins by means of the Mitsunobu reaction is also described.
About the journal
JournalEuropean Journal of Organic Chemistry
ISSN1434193X
Open AccessNo
Concepts (13)
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    Benzene
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    Chromene derivative
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    Deuterium
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    Ether derivative
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    Pterocarpan derivative
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    Tributyltin
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    Unclassified drug
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    Article
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    Cyclization
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    Isotope labeling
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    Reaction analysis
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    Stereochemistry
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    Synthesis