A cycloisomerization/Friedel-Crafts alkylation strategy for the synthesis of pyrano[3,4-b]indoles |
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| Authors: | Medeiros Matthew R Schaus Scott E Porco John A |
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| Affiliation: | Chemistry Department, Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA. |
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| Abstract: | The synthesis of pyrano[3,4-b]indoles is described. The reaction sequence involves Sonogashira coupling of dihydropyran propargyl ether scaffolds with iodoanilines to afford intermediate indoles. Lewis acid-catalyzed ionization of the dihydropyrans, followed by intramolecular C3 alkylation of the indole, provides the title compounds. |
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