Assignment of the 1H and 13C NMR spectra of the quinolizidine alkaloid anagyrine and determination of its conformation

Rycroft, D. S., Robins, D. J. and Sadler, I. H. (1991) Assignment of the 1H and 13C NMR spectra of the quinolizidine alkaloid anagyrine and determination of its conformation. Magnetic Resonance in Chemistry, 29(9), pp. 936-940. (doi: 10.1002/mrc.1260290913)

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Abstract

The 1H NMR spectrum of the quinolizidine alkaloid (−)-anagyrine has been studied at 200 and 600 MHz. A full assignment of the 1H signals has been achieved by application of a variety of NMR techniques, including homonuclear spin decoupling, NOE difference, 2D δH/δH COSY and direct δC/δH correlation (including HMQC) experiments. The 13C NMR spectrum has also been assigned, and differences from the current literature assignments are reported. The conformation of (−)-anagyrine has been elucidated by consideration of the proton-proton spin-spin coupling constants and NOEs. The configuration of the lone pair of the tertiary amine nitrogen is β, ring B has an envelope conformation and rings C and D have chair conformations with a cis-decalin type of ring fusion between them.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Rycroft, Dr David and Robins, Prof David
Authors: Rycroft, D. S., Robins, D. J., and Sadler, I. H.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Magnetic Resonance in Chemistry
Publisher:John Wiley & Sons, Ltd
ISSN:0749-1581
ISSN (Online):1097-458X

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