Very short and efficient syntheses of the spermine alkaloid kukoamine A and analogs using isolable succinimidyl cinnamates

TY - JOUR

T1 - Very short and efficient syntheses of the spermine alkaloid kukoamine A and analogs using isolable succinimidyl cinnamates

AU - Garnelis, Thomas

AU - Athanassopoulos, Constantinos M.

AU - Papaioannou, Dionissios

AU - Eggleston, Ian M.

AU - Fairlamb, Alan H.

PY - 2005/2/5

Y1 - 2005/2/5

N2 - Direct selective acylation of the primary amino functions of spermine and spermidine with a variety of isolable succinimidyl cinnamates, followed by catalytic hydrogenation, gave high yields of the spermine alkaloid kukoamine A and analogs suitable for structure-activity relationship studies. Suitable succinimidyl cinnamates were readily obtained through Wittig reaction of aromatic aldehydes with the ylides Ph3P=CRCO2Me, followed by saponification and activation with N-hydroxysuccinimide in the presence of N,N'-dicyclohexylcarbodiimide.

AB - Direct selective acylation of the primary amino functions of spermine and spermidine with a variety of isolable succinimidyl cinnamates, followed by catalytic hydrogenation, gave high yields of the spermine alkaloid kukoamine A and analogs suitable for structure-activity relationship studies. Suitable succinimidyl cinnamates were readily obtained through Wittig reaction of aromatic aldehydes with the ylides Ph3P=CRCO2Me, followed by saponification and activation with N-hydroxysuccinimide in the presence of N,N'-dicyclohexylcarbodiimide.

UR - https://www.scopus.com/pages/publications/17844364447

U2 - 10.1246/Cl.2005.264

DO - 10.1246/Cl.2005.264

M3 - Article

AN - SCOPUS:17844364447

SN - 0366-7022

VL - 34

SP - 264

EP - 265

JO - Chemistry Letters

JF - Chemistry Letters

IS - 2

ER -