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The Macrocyclic Spermidine Alkaloid (−)-(S)-Neoperiphylline: Revision of the Structure Based on the Total Synthesis

✍ Scribed by Sergey A. Sergeyev; Manfred Hesse

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
109 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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 (−)‐(4__S__,12__Z__)‐4‐phenyl‐9‐[(2__E__)‐3‐phenylprop‐2‐enoyl]‐1,5,9‐triazacyclotridec‐12‐en‐2‐one (17).

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