First Direct and Detailed Stereochemical Analysis of Strictosidine

Using the easy lactamization of vincoside (4), epimer-free strictosidine (1) was prepared from secologanin (2) and tryptamine (3). 2D NMR methods were used to determine unambiguously the 1H- and 13C-NMR chemical shifts, the 1H−H and 13C−1H coupling constants, and the 1H−1H NOE interactions in strict...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1997-02, Vol.60 (2), p.69-75
Main Authors: PATTHY-LUKATS, A, KAROLYHAZY, L, SZABO, L. F, PODANYI, B
Format: Article
Language:English
Subjects:
alcaloide
alcaloides
Alicyclic compounds, terpenoids, prostaglandins, steroids
alkaloids
apocynaceae
chemical composition
chemical structure
Chemistry
chimie
composicion quimica
composition chimique
espectrometria
estructura quimica
Exact sciences and technology
glicosidos
glycoside
glycosides
indol
indoles
monoterpene
monoterpenes
monoterpenos
Organic chemistry
Preparations and properties
purificacion
purification
quimica
spectrometrie
spectrometry
structure chimique
Terpenoids
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Summary:Using the easy lactamization of vincoside (4), epimer-free strictosidine (1) was prepared from secologanin (2) and tryptamine (3). 2D NMR methods were used to determine unambiguously the 1H- and 13C-NMR chemical shifts, the 1H−H and 13C−1H coupling constants, and the 1H−1H NOE interactions in strictosidine (1). A minimal number of spectroscopic parameters (11 coupling constants, 3 NOEs) and some theoretical considerations have made it possible to select the single species of the 648 selected stereoisomers and to confirm directly the S configuration at the newly formed C-3 chiral center, the P helicity of the dihydropyran and tetrahydropyridine rings, and the conformations around C-14 and the glycosidic bridge.
ISSN:0163-3864
1520-6025
DOI:10.1021/np960324u