Showing papers by "Sergey Sergeyev published in 2002"
TL;DR: In this article, a short and highly stereoselective synthesis of the macrocyclic spermidine alkaloid (+)-(S)-dihydroperiphylline (15) is described.
Abstract: A novel, short, and highly stereoselective synthesis of the macrocyclic spermidine alkaloid (+)-(S)-dihydroperiphylline (15) is described. The key synthetic steps were the stereoselective addition of the chiral amine 1 to the cinnamate 2 and cyclization of the bis[toluene-4-sulfonamide] precursor 12 in the presence of Cs2CO3 as a template. Unambiguous assignments of the signals in both the 1H- and 13C-NMR spectra of 15 were achieved by 2D NMR spectra.
8 citations
TL;DR: Isomerization of various N-allylamides in the presence of Fe(CO) 5 smoothly afforded the corresponding enamides in yields up to 95% as discussed by the authors, which is compatible with various functional groups including protected amino and hydroxy groups.
Abstract: Isomerization of various N-allylamides in the presence of Fe(CO) 5 smoothly afforded the corresponding enamides in yields up to 95%. The reported procedure is compatible with various functional groups including protected amino and hydroxy groups. The possible mechanism of transformation is discussed.
6 citations
TL;DR: Isomerization of various N-allylamides in the presence of Fe(CO) 5 smoothly afforded the corresponding enamides in yields up to 95% as discussed by the authors, which is compatible with various functional groups including protected amino and hydroxy groups.
Abstract: Isomerization of various N-allylamides in the presence of Fe(CO) 5 smoothly afforded the corresponding enamides in yields up to 95%. The reported procedure is compatible with various functional groups including protected amino and hydroxy groups. The possible mechanism of transformation is discussed.
1 citations
TL;DR: In this paper, a short and highly stereoselective synthesis of the macrocyclic spermidine alkaloid (+)-(S)-dihydroperiphylline (15) is described.
Abstract: A novel, short, and highly stereoselective synthesis of the macrocyclic spermidine alkaloid (+)-(S)-dihydroperiphylline (15) is described. The key synthetic steps were the stereoselective addition of the chiral amine 1 to the cinnamate 2 and cyclization of the bis[toluene-4-sulfonamide] precursor 12 in the presence of Cs2CO3 as a template. Unambiguous assignments of the signals in both the 1H- and 13C-NMR spectra of 15 were achieved by 2D NMR spectra.