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.

HEXACYCLIC INDOLE ALKALOIDS - THE STRUCTURE OF CUANZINE AS AN EXPERIMENTAL TEST OF MOLECULAR MECHANICS CALCULATIONS / G. PALMISANO, B. GABETTA, G. LESMA, T. PILATI, L. TOMA. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 55:7(1990), pp. 2182-2185.

HEXACYCLIC INDOLE ALKALOIDS - THE STRUCTURE OF CUANZINE AS AN EXPERIMENTAL TEST OF MOLECULAR MECHANICS CALCULATIONS

G. LESMA;
1990

Abstract

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.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/183734
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