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Total assignment of the proton and carbon NMR spectra of 5′‐NOR‐anhydrovinblastine
Author(s) -
Spitzer Timothy D.,
Crouch Ronald C.,
Martin Gary E.
Publication year - 1992
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.5570290151
Subject(s) - geminal , homonuclear molecule , chemistry , methylene , carbon 13 nmr , chemical shift , spectral line , stereochemistry , proton , diastereomer , analytical chemistry (journal) , nuclear magnetic resonance , molecule , organic chemistry , nuclear physics , physics , astronomy
Total spectral assignment of the bis‐indole alkaloid Navelbine®, 5′‐nor‐anhydrovinbIastine, was accomplished using a combination of two‐dimensional nmr techniques. Conventional homonuclear and inverse‐detected experiments were supplemented with the HMQC‐TOCSY experiment to unequivocally assign carbons directly bound to overlapped protons. In addition, the recently introduced GEM‐COSY experiment was evaluated as a technique for the identification of geminal methylene pairs. Partial assignments proposed by Potier and co‐workers, based on chemical shift considerations, are largely in agreement with the unequivocal assignments determined in this study.