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The macrocyclic spermidine alkaloid (-)-(S)-neoperiphylline: Revision of the structure based on the total synthesis

par Sergueev, Serguei ;Hesse, Manfred
Référence Helvetica chimica acta, 86, 2, page (465-473)
Publication Publié, 2003

Article révisé par les pairs

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Résumé :

The total synthesis of the two isomeric macrocyclic enamides 2 and 17 is described. The precursor 14 was synthesized by means of template-assisted macrocyclization (Scheme 2). Isomerization of 14 in the presence of [Fe(CO)5] gave 2 and 17 (Scheme 4). Structure 2 was previously assigned to the alkaloid neoperiphylline. However, the synthetic 2 showed completely different properties compared to the earlier described data of the natural compound. Surprisingly, analytical data of the second synthetic product 17 were very close to those of the natural neoperiphylline. We conclude that the previously assigned structure of neoperiphylline is erroneous and should be corrected to that of (-)-(4S,12Z)-4-phenyl-9- [(2E)-3-phenylprop-2-enoyl]-1,5,9-triazacyclotridec-12-en-2-one (17).