31035-84-4Relevant academic research and scientific papers
Synthesis of the macrocyclic spermidine alkaloid (±)-(2R*,3R*)-3-hydroxycelacinnine
Khanjin, Nikolai A.,Hesse, Manfred
, p. 1253 - 1267 (2007/10/03)
The macrocyclic lactam alkaloid (±)-(2R*,3R*)-3-hydroxycelacinnine (1) derived from spermidine was synthesized via stereoselective epoxide-ring opening with magnesium azide and cesium carbonate promoted macrocyclization of the ditosylated diamino precursor 12 with 1,4-dibromobutane in the two key steps (Scheme 2). 1H- and 13C-NMR Signal assignments from COSY, HSQC, and HMBC 2D NMR data of the synthesized 1 were compared with the earlier-described data of the natural 3-hydroxycelacinnine. The similarity of their 13C-NMR spectra point to the correctness of the proposed constitutional formula for natural 3-hydroxycelacinnine; however, different 1H-NMR chemical shifts and coupling constants (J(2,3) = 9.0 vs. 1.2 Hz, resp.) in the α-hydroxy-β-amino lactam moiety suggest that natural 3-hydroxycelacinnine is the 2,3-cis-epimer of one synthetic (±)-1.
