Syntheses and Chiroptical Properties of the 13-Membered Spermidine Alkaloids (-)-(S)-Celacinnine, (0)-(S)-Celabenzine, (-)-(S)-Celafurine, and (+)-(S)-Viburnine.

The title alkaloids were prepared from the common chiral precursor (−)-(2S)-2-phenyl-1, 5, 9-triazacy-clotridecan-4-one (4) which we had synthesized earlier. The spectral data for the spermidine macrocycles are in good agreement with the data reported for the isolated samples. Our experimental results indicate that the originally reported [α]D value of −2.6 (c = 0.10, MeOH) for natural (S)-viburnine is erroneous and should be + 17.0 (c = 0.92, MeOH). As a result of the chiroptical study conducted, it can be shown empirically that all alkaloids of the ‘celacinnine’ type have the (S)-configuration.