The conformational space of cuanzine was explored by employing MM2 force field for energy calculations and minimization. Location of the global minimum on the potential energy surface furnished a geometry which resembles the literature reported X-ray conformation of vincamine 3. Moreover, the global minimum of structure 1 was found at a higher energy value than the global minimum of its C(16) epimer 8, suggesting that the previous assignment of structure 1 to natural cuanzine should be revised into 8. Reinterpretation of the 1H NMR data reinforced this suggestion which was ultimately confirmed by X-ray analysis of cuanzine hydrochloride.
|Titolo:||HEXACYCLIC INDOLE ALKALOIDS - THE STRUCTURE OF CUANZINE AS AN EXPERIMENTAL TEST OF MOLECULAR MECHANICS CALCULATIONS|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||1990|
|Digital Object Identifier (DOI):||10.1021/jo00294a037|
|Appare nelle tipologie:||01 - Articolo su periodico|