Polar Control of the Regioselectivity of Hetaryne Cycloadditions. Synthesis of Ellipticine

M. Teresa Díaz; Agustín Cobas; Enrique Guitián; Luis Castedo

doi:10.1055/s-1998-1607

Synlett 1998; 1998(2): 157-158
DOI: 10.1055/s-1998-1607

letter

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

PDF Download All articles of this category

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

PDF (33 kb)