Solid phase syntheses of polyamine toxins HO-416b and PhTX-433. Use of an efficient polyamide reduction strategy that facilitates access to branched analogues.
[structure--se text] Polyamine toxins HO-416b (1) and PhTX-433 (2) isolated from the venom of insects are important lead compounds in neuropharmacology. Their total synthesis has been achieved on a trityl derivatized resin in good yield and purity using a mild borane reduction protocol to access the polyamine chains from polyamide precursors. The synthesis of PhTX isomer 3 demonstrates the potential of this strategy for the generation of branched analogues.
Wang
F
F
Department of Chemistry, University of Alberta, Edmonton, Canada.
Manku
S
S
Hall
D G
DG
D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D009498:Neurotoxins / Q000138:chemical synthesis / Q000737:chemistry*; D018733:Nicotinic Antagonists / Q000138:chemical synthesis / Q000737:chemistry; D011073:Polyamines / Q000138:chemical synthesis / Q000737:chemistry*; D013111:Spider Venoms / Q000138:chemical synthesis / Q000737:chemistry; D014862:Wasp Venoms / Q000138:chemical synthesis / Q000737:chemistry
C410205:HO 416b; D007211:Indoles; D009498:Neurotoxins; D018733:Nicotinic Antagonists; D011073:Polyamines; D013111:Spider Venoms; D014862:Wasp Venoms; C034092:delta-philanthotoxin