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Long‐range 1 H‐ 15 N two‐dimensional heteronuclear shift correlation of the alkaloid vincamine at natural abundance
Author(s) -
Martin Gary E.
Publication year - 1997
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570340261
Subject(s) - chemistry , heteronuclear molecule , abundance (ecology) , alkaloid , range (aeronautics) , stereochemistry , nuclear magnetic resonance spectroscopy , fishery , biology , materials science , composite material
Abstract Long‐range 1 H‐ 15 N heteronuclear correlation pathways in the alkaloid vincamine, a structural constituent or biogenetic congener of numerous Vinca alkaloids, are reported. Correlations were observed through the use of the GHNMQC (Gradient‐enhanced Hydrogen‐Nitrogen Multiple Quantum Coherence) 2D nmr experiment at natural abundance. An unanticipated four‐bond coupling between the H15a resonance and N4 was observed in contrast to the typical two‐ and three‐bond coupling pathways. Nitrogen‐15 chemical shift comparisons are drawn between vincamine and structurally related alkaloids including ajmaline and the velbanamine portion of the semi‐synthetic alkaloid vinorelbine (Navelbine TM ).