Total Synthesis of (+/-)-15-Deoxyspergualin

Article abstract of DOI:10.1021/jo00385a010

The synthesis of (+/-)-7<(aminoiminomethyl)amino>-N-<2-<<4-<(3-aminopropyl)amino>butyl>amino>-1-hydroxy-2-oxoethyl>heptanamide trihydrochloride, (+/-)-15-deoxyspergualin, 2b, a potent antitumor and antibiotic spermidine alkaloid, is reported.The synthesis is predicated on the development of the protected spermidine N¹,N⁴-bis(tert-butoxycarbonyl)spermidine (12) and guanidine reagent N,N'-bis(tert-butoxycarbonyl)-S-methylisothiourea (18).The sensitive alkanolamide moiety of (+/-)-15-deoxyspergualin ( C-11 in 2b ) is formed and then protected as its tert-butyldimethylsilyl ether in 21.The reactive ester group of 21 undergoes aminolysis with 12 to from protected deoxyspergualin 22.All of the protecting groups in 22 are removed by trifluoroacetic acid to furnish final product 2b.