Solid-phase synthesis of polyamines using a Dde-linker: philanthotoxin-4.3.3 via an on-resin Mitsunobu reaction
2000; Elsevier BV; Volume: 41; Issue: 7 Linguagem: Inglês
10.1016/s0040-4039(99)02239-x
ISSN1873-3581
AutoresSiri Ram Chhabra, Azra N Khan, Barrie W. Bycroft,
Tópico(s)Polyamine Metabolism and Applications
ResumoA Dde linker/solid-phase procedure for the stepwise construction of polyamines is illustrated with the synthesis of philanthotoxin-4.3.3. Resin-bound 4-aza-1,7-heptanediamine was N4-protected and N7-activated in a single operation with 2-nitrobenzenesulphonyl chloride. Alkylation with N-Fmoc-4-aminobutanol under Mitsunobu conditions completed the polyamine backbone. Deprotection of the sulphonamide groups was readily achieved with thiolates in DMF at room temperature.
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