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Mass spectrometry in structural and stereochemical problems. The structure of the aspidosperma alkaloid aspidoalbine

✍ Scribed by Cari Djerassi; L.D. Antonaccio; H. Budzikiewicz; J.M. Wilson; B. Gilbert

Publisher
Elsevier Science
Year
1962
Tongue
French
Weight
441 KB
Volume
3
Category
Article
ISSN
0040-4039

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✦ Synopsis

IN continuation of our studies3 on the alkaloidal constituents of Brazilian Aspidosperma species, we have investigated the stem bark of Aspidosperma album (Vahl) R. Bent., which was collected in Manaus, Amaronas. The non-phenolic portion yielded the lcnown alkaloid4 (-)-quebmchamine, while from the phenolic fraction there was isolated a new alkaloid, arpidaalbine, for which we propose structure I, largely on the basis of mass spectral and n.m.r. evidence. Aspidoalbine (I) is the first (dihydro) indole alkaloid in which three of the four aromatic hydrogens are replaced by oxygen functions and it is also the first alkaloid based on an aspidospermine-like skeletons in which the presence of a tetrahydrofuran ring could be demonstrated.

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