Syntheses and Chiroptical Properties of the 13‐membered spermidine alkaloids (−)‐(S)‐celacinnine, (0)‐(S)‐celabenzine, (−)‐(S)‐celafurine, and (+)‐(S)‐viburnine

作者: Paul Kuehne , Armin Guggisberg , Manfred Hesse

DOI: 10.1002/HLCA.19970800604

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摘要: 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. spectral data for spermidine macrocycles are in good agreement with reported isolated samples. Our experimental results indicate that originally [α]D value of −2.6 (c = 0.10, MeOH) natural (S)-viburnine is erroneous and should be + 17.0 0.92, MeOH). As a result chiroptical study conducted, it can shown empirically all ‘celacinnine’ type have (S)-configuration.

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