Showing papers by "Sergey Sergeyev published in 2003"
TL;DR: In this article, a method for preparation of enamides (N-(alken-1-yl) amides) by means of the "long-distance" migration of the double bond in unsaturated amides in the presence of [Fe(CO)5] is described.
Abstract: A new method for preparation of enamides (N-(alken-1-yl) amides) by means of the ‘long-distance' migration of the double bond in unsaturated amides in the presence of [Fe(CO)5] is described. The method is shown to be particularly useful for the isomerization of N-(but-3-enyl)amides, while, in the case of N-(pent-4-enyl) and N-(hex-5-enyl) amides the mixture of products was formed and the yield of the enamide was relatively low.
14 citations
TL;DR: The total synthesis of the two isomeric macrocyclic enamides 2 and 17 is described in this paper, where the precursor 14 was synthesized by means of template-assisted macrocyclization and the structure 2 was previously assigned to the alkaloid neoperiphylline.
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 (-)-(4S,12Z)-4-phenyl-9- [(2E)-3-phenylprop-2-enoyl]-1,5,9-triazacyclotridec-12-en-2-one (17)
5 citations
TL;DR: In this paper, the total synthesis of the two isomeric macrocyclic enamides 2 and 17 is described and the analytical data of the second synthetic product 17 were very close to those of the natural neoperiphylline.
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 (-)-(4S,12Z)-4-phenyl-9- [(2E)-3-phenylprop-2-enoyl]-1,5,9-triazacyclotridec-12-en-2-one (17).