N2,N3-DI-TERT-BUTOXYCARBONYLSPERMIDINE - SYNTHESIS OF THE AGLYCONE OF THE LL-BM123 ANTIBIOTICS

In recent years several alkaloids have been discovered that have spermidine (1) incorporated in their structures.2 As part of our plan to synthesize several of these alkaloids, we required a derivative of spermidine in which the secondary amine and one of the primary amines were blocked by a group that is stable to base and to other vigorous, nonacidic conditions. Because the ieri-butoxycarbonyl (BOC) group constitutes a base-stable, acid-labile nitrogen protecting group,3 N2, N3-di-terf-butoxycarbonylspermidine (2) was prepared.4. Cyclohexylamine. © 1979, American Chemical Society. All rights reserved.