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Remarkable switch of regioselectivity in diels-alder reaction: Divergent total synthesis of borreverine, caulindoles, and flinderoles
D.H. Dethe, , B.D. Dherange
Published in American Chemical Society
PMID: 24797220
Volume: 16
Issue: 10
Pages: 2764 - 2767
Switchable reaction patterns of dimerization of indole substituted butadienes via a Lewis acid and thermal activation are reported. While under acidic conditions dimerization occurred around the internal double bond of the dienophile, a complete switch of regioselectivity was observed under thermal conditions, where dimerization occurred around the terminal double bond of the dienophile. This switch of regioselectivity was further exploited for the divergent total synthesis of structurally diverse indole alkaloid natural products. © 2014 American Chemical Society.
About the journal
JournalData powered by TypesetOrganic Letters
PublisherData powered by TypesetAmerican Chemical Society