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Structure elucidation of the binary indole alkaloid uncaramine

The structure elucidation of uncaramine (1), a binary alkaloid derived from gambirine and pseudoyohimbine moieties linked together through a C(10)–C(21′) bond, has been performed mainly using 1H and 13 n.m.r. spectroscopy. The presence of a hydrogen bond between the 9-hydroxy proton and the 4′-nitrogen atom established a preferred orientation of the two halves, the C(11)–C(10)–C(21′)–H(21′) dihedral angle being ca. 20°. A complete assignment for the 1H n.m.r. spectrum of gambirine (2) is also presented.