The Structure of Vincarodine

Abstract

The structure of vincarodine has been determined to be 1 by an investigation of its IR.‐, UV.‐, 1H‐ and 13C‐NMR.‐ and mass spectra. A 13C‐NMR. analysis has been performed on the bases vincamine (2), epivincine (9), 14, 15‐dehydrovincine (7) and its 16‐epimer (8).

The Use of Carbon-13 Nuclear Magnetic Resonance Spectroscopy in Natural Products Chemistry

“…I3C spectral data have recently been reported for strychnine (670) and brucine (671) as well as for their ions, obtained upon addition of trifluoroacetic acid (177). Although an earlier I3C analysis of brucine (58) made use of similar arguments, a discrepancy remains in the assignments of C-Il, C-18 and C- 20. In the course of a structural study of vincarodine (672), its 13C spectrum was analyzed (178). Tn model amines and amides it was found that amino and amido protonation induces upfield and downfield shifts, resp., on the adjacent carbons.…”

“…and the related compounds (674----676)(178,179). 13C spectroscopy was employed in structure investigations of pandine (677) and its derivative (678) (180), andraginine (679)(181) as well as the rearrangement product (680) from catharanthine N-oxide (182).CO,M.…”

Discovery of a P450-catalyzed step in vindoline biosynthesis: a link between the aspidosperma and eburnamine alkaloids

“…2). 16 Previous reports indicate that 2-imine, 3-alcohols on the tabersonine framework can undergo facile acid catalyzed rearrangement to the eburnamine-vincamine skeleton (Fig. 2).…”

Monoterpene Indole Alkaloids with Cav3.1 T-Type Calcium Channel Inhibitory Activity from Catharanthus roseus

“…The total crude alkaloid fraction was subjected to MCI gel, silica gel, and Sephadex LH-20 to afford two new MIAs, catharanosines A (1) and B (2), and six known analogues. Compared with literature data, the known compounds were identified as (R)-19-hydroxytabersonine (3) [24], lochnerine (4) [25], normacusine B (5) [26], vincapusine (6) [27], vincarodine (7) [28], and serpentine (8) [29], by comparing their spectroscopic data with those reported in the literature.…”