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- W2321710400 abstract "Two benzyltetrahydroisoquinoline−protoberberine dimers, longiberine (1) and O-methyllongiberine (2), were isolated from the roots of Thalictrum longistylum and represent a new class of dimeric alkaloids. The structure of longiberine (1) was established by spectral and chemical methods. Reductive cleavage of O-ethyllongiberine (4) with Na/liquid NH3 yielded (+)−(S)-N-methylcoclaurine (5), which determined one-half of the dimer, and 1D and 2D NMR studies arranged the substituents on the protoberberine nucleus. Chemical conversion of thalidezine (6) to 1 via the O-acetyl N,N-didemethyl derivative 9, which was methylenated in the Mannich reaction and N-methylated by the Eschweiler−Clarke procedure, established the second asymmetric center as S and confirmed the ring size and the order of the substituents for 1. Methylation of 1 with diazomethane formed the O-methyl derivative 2, identical with the natural product." @default.
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- W2321710400 date "1999-09-14" @default.
- W2321710400 modified "2023-10-03" @default.
- W2321710400 title "Longiberine and <i>O</i>-Methyllongiberine, Dimeric Protoberberine-Benzyl Tetrahydroisoquinoline Alkaloids from <i>Thalictrum </i><i>l</i><i>ongistyl</i><i>um</i>" @default.
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- W2321710400 doi "https://doi.org/10.1021/np9902284" @default.
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