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Synlett 1998; 1998(2): 157-158
DOI: 10.1055/s-1998-1607
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Polar Control of the Regioselectivity of Hetaryne Cycloadditions. Synthesis of Ellipticine

M. Teresa Díaz* , Agustín Cobas, Enrique Guitián, Luis Castedo
  • *Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago, 15706 Santiago de Compostela, Spain
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Publikationsdatum:
31. Dezember 2000 (online)

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A regioselective cycloaddition between 1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole and 2-chloro-3,4-didehydropyridine is the key step of a modification of Gribble's approach to ellipticines. The use of a fluoride-promoted elimination for the generation of the pyridyne and the control of the regioselectivity of the cycloaddition improve the yield of ellipticine by a factor of 3.

ellipticine - 2-chloro-3,4-didehydropyridine - pyridyne cycloaddition