The absolute molecular structure of hodgkinsine (cas 18210-71-4)

Add time:07/30/2019    Source:sciencedirect.com

Preliminary crystallographic analysis of crystals of the respective benzene and bromobenzene adducts of hodgkinsine, an alkaloid from Hodgkinsonia frutescens F. Muell. (family Rubiaceae), together with mass spectral evidence suggested a formulation for hodgkinsine based on three N-methyltryptamine units. X-ray analysis of crystals of the trimethiodide monohydrate, C33H38N6.3CH3I.H2O, has defined the absolute molecular structure of hodgkinsine. These crystals are monoclinic belonging to the space group P21, with a = 12·779, b = 13·923, c = 11·190 Å, β = 107·78°, Z = 2. The crystal structure has been solved from data collected with CuKα radiation on a single-crystal diffractometer and refined by least-squares procedures from intensity data re-collected with MoKα radiation. The absolute chirality was defined by Bijvoet's technique. The molecular structure of hodgkinsine is given as I. Two of the N-methyltryptamine units T″ and T″' are in the same configuration while T′ is in the opposite. The CD spectrum of hodgkinsine is discussed in relation to these units of different chiralities.

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