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Benzo- and indoloquinolizine derivatives. VI—configuration and conformation of 4b,5,6,7,8,8a,10,11,16,16b-decahydrodibenz[f,h]indolo[2,3-a]quinolizine diastereoisomers. A 270 MHz 1H NMR study

✍ Scribed by G. van Binst; D. Tourwé

Publisher
John Wiley and Sons
Year
1974
Tongue
English
Weight
554 KB
Volume
6
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The synthesis of a D/E cis isomer of the title compound is described. In an attempt to obtain the other D/E cis isomer, epimerisation reactions were studied. The configuration and conformation of the isomers are determined on the basis of their ^1^H NMR spectra. The shift of the 16b proton on N‐9 protonation indicates the quinolizidine conformation. At 270 MHz, the ABCD system of the C‐10 and C‐11 methylenes can be analysed. The ^2^J(C‐10H~2~), together with the multiplicity of H‐8a, allows an unequivocal assignment of a cis‐anti‐cis structure to the only D/E cis isomer obtained.

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