186179-24-8Relevant articles and documents
A novel synthesis of the macrocyclic spermidine alkaloid (+)-(S)-dihydroperiphylline
Sergeyev, Sergey A.,Hesse, Manfred
, p. 161 - 167 (2002)
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 o
178. Electrospray-ionization mass spectrometry part III: Acid-catalyzed isomerization of N,N′-bis[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]spermidines by the Zip reaction
Bigler, Laurent,Schnider, Christian F.,Hu, Wenqing,Hesse, Manfred
, p. 2152 - 2163 (2007/10/03)
The electrospray tandem mass spectra (ESI-MS/MS) of the three N,N′-bis[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]spermidines 1-3 displayed the same fragment-ion signals. These isomers could not be differentiated by ESI-MS/MS, since their fragmentation patterns are similar. (E,E)-N-(3-[ 15N]Aminopropyl)-3,3′-bis(4-hydroxyphenyl)-N,N′-(butane- 1,4-diyl)bis[prop-2-enamide] ([15N(1)]-1) was synthesized in order to get further information about the fragmentation mechanisms. The comparison of the ESI-MS/MS of 1 and [15N(1)]-1 revealed a transamidation, the Zip reaction, under mass-spectral conditions of the [1 + H]+ ions. Because of this reaction, the three isomers 1-3 could not be distinguished.