Solid-phase synthesis of polyamines using a Dde-linker: Philanthotoxin- 4.3.3 via an on-resin Mitsunobu reaction

Article abstract of DOI:10.1016/S0040-4039(99)02239-X

A 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. (C) 2000 Elsevier Science Ltd.