The Journal of Organic Chemistry

Chemistry of naturally occurring polyamines. 10. Nonmetabolizable derivatives of spermine and spermidine

S Nagarajan, B Ganem

Index: Nagarajan, Srinivasan; Ganem, Bruce Journal of Organic Chemistry, 1986 , vol. 51, # 25 p. 4856 - 4861

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Citation Number: 52

Abstract

-8 ir excess 1, 4-diaminobutane using the mixed-anhydride method (CICOzEt, Et3N, THF) furnished azido amide 17 (72%). However, reduction of the amide group in this substance proved troublesome and gave at best 30-35% of spermidine 8. To solve this problem, 16 was first reduced with B2H6 and then oxidized with pyridinium dichromate (PDC) to azido aldehyde 18, which smoothly condensed12 with 1, 4-diaminobutane (Pt02-H2, EtOH) to ...