Tetrahedron p. 11601 - 11608 (1999)
Update date:2022-08-17
Topics:
Cavazza, Marino
Nucci, Lamberto
Pannocchia, Elisa
Pardi, Lucio
Pergola, Francesco
Pinzino, Calogero
Pietra, Francesco
Colchicine (1), a potently antimitotic alkaloid and useful laboratory tool in cancer research, undergoes cathodic reduction in DMF forming an ESR- observable radical anion (1r) which is characterized by the isotropic hyperfine coupling constants 8.9, 4.3, 0.75, 0.49 and 0.48 G for H-8, H-12, OCH3, H-11 and H-4, respectively, and a much flattened troponoid ring. Assignments are aided by selective deuteriation of colchicine at C-8, C-11 and COCH3, as well as by spectral simulation and ab initio calculations of electron spin densities. Whether the colchicine radical anion may exist in nature is also discussed.
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