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

✍ Scribed by David S. Rycroft; David J. Robins; Ian H. Sadler

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
430 KB
Volume
29
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The ^1^H NMR spectrum of the quinolizidine alkaloid ( − )‐ anagyrine has been studied at 200 and 600 MHz. A full assignment of the ^1^H signals has been achieved by application of a variety of NMR techniques, including homo‐nuclear spin decoupling, NOE difference, 2D δ~H~/δ~H~ COSY and direct δ~c~/δ~H~ correlation (including HMQC) experiments. The ^13^C 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 cis‐decalin type of ring fusion between them.

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