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Synthesis of Pterocarpans by Means of a “Disfavored” 5-endo-trig Radical Cyclization Reaction

✍ Scribed by Kalpathy Chidambareswaran Santhosh; Ariamala Gopalsamy; Kalputtu Kuppuswamy Balasubramanian

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
285 KB
Volume
2001
Category
Article
ISSN
1434-193X

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✦ Synopsis

A successful synthesis of pterocarpans 1, based on a ''disfavored'' 5-endo-trig radical cyclization reaction, has been accomplished. The radical precursor 4-(2Ј-bromoaryloxy)-2Hchromene 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 [a

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