Two Dibenzopyrrocoline Alkaloids from Litsea cubebaClick to copy article linkArticle link copied!
Abstract
Further investigation of quaternary alkaloids from Litsea cubeba led to the isolation of two novel dibenzopyrrocoline alkaloids, (−)-litcubine (1) and (−)-litcubinine (2). Their structures and 7R,13S stereochemistry were elucidated by spectral analysis and chemical correlation. Including these two, only six dibenzopyrrocoline alkaloids have been isolated from natural sources.
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Abstract published in Advance ACS Abstracts, December 1, 1995.
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(7)
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(4)
, 387. https://doi.org/10.1039/np9971400387
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