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Synthesis of the Macrocyclic Spermidine Alkaloid (±)-(2R*,3R*)-3-Hydroxycelacinnine

✍ Scribed by Nikolai A. Khanjin; Manfred Hesse

Publisher
John Wiley and Sons
Year
2001
Tongue
German
Weight
168 KB
Volume
84
Category
Article
ISSN
0018-019X

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✦ Synopsis

Dedicated to Edgar Heilbronner on the occasion of his 80th birthday

The macrocyclic lactam alkaloid (AE)-(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). 1 H-and 13 C-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 13 C-NMR spectra point to the correctness of the proposed constitutional formula for natural 3hydroxycelacinnine; however, different 1 H-NMR chemical shifts and coupling constants (J(2,3) 9.0 vs. 1.2 Hz, resp.) in the a-hydroxy-b-amino lactam moiety suggest that natural 3-hydroxycelacinnine is the 2,3-cis-epimer of one synthetic (AE)-1.

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