A sequential high-yielding large-scale solution-method for synthesis of philanthotoxin analogues
Research output: Contribution to journal › Journal article › Research › peer-review
A general, improved procedure for rapid synthesis of philanthotoxin analogues, a pharmacologically important class of polyamine conjugates, is described. The solution-phase procedure is illustrated by gram-scale synthesis of philanthotoxins PhTX-343 and PhTX-12. Selectively protected polyamines are coupled to N(alpha)-Fmoc-protected amino acid pentafluorophenyl esters. After removal of the N(alpha)-Fmoc group, the amine is coupled with carboxylic acid pentafluorophenyl esters. Deprotection followed by a rapid and efficient purification by vacuum liquid chromatography on octadecylsilyl silica (RP-18 phase) gave the philanthotoxin analogues in 74-78% overall yield.
Original language | English |
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Journal | European Journal of Medicinal Chemistry |
Volume | 38 |
Issue number | 1 |
Pages (from-to) | 117-22 |
Number of pages | 6 |
ISSN | 0223-5234 |
Publication status | Published - 2003 |
- Chromatography, Liquid, Combinatorial Chemistry Techniques, Electrophoresis, Capillary, Magnetic Resonance Spectroscopy, Models, Chemical, Phenols, Polyamines, Silica Gel, Silicon Dioxide, Solutions, Tyrosine
Research areas
ID: 42389845