Structure elucidation and chemistry of Catharanthus alkaloids. XXX. Isolation and structure elucidation of vincarodine

The Journal of Organic Chemistry
1974.0

Abstract

Continuing work on antileukemic alkaloids of Catharanthus roseus led to the isolation of vincarodine from the post-VLB-pre-VCR fraction via pH gradient fractionation. Physicochemical analyses (IR, NMR, mass spectrometry) and chemical reactions (acetylation, reduction) were used to elucidate its structure. High-resolution mass spectrometry determined the molecular formula as C22H26N2O5 (molecular weight 398), correcting a previous dimeric proposal. Structural studies revealed an Eburna-type skeleton with a novel ether linkage, a hydroxy group at C-14, and a trans (diaxial) relationship between the oxygen atoms at C-14 and C-15. Mass spectral fragmentation patterns (e.g., base peak at m/e 200) and NMR data (including solvent shift and acetylation experiments) supported the assignment of structure 9 or its mirror image.

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