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Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis

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2005
Authors
Bjelaković, Mira
Krstić, Natalija
Tinant, Bernard
Kalvoda, Jaroslav
Csanadi, Janos
Pavlović, Vladimir D.
Article (Published version)
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Abstract
The conformations of (Z)‐ and (E)‐5‐oxo‐B‐nor‐5,10‐secocholest‐1(10)‐en‐3β‐yl acetates (2 and 3, resp.) were examined by a combination of X‐ray crystallographic analysis and NMR spectroscopy, with emphasis on the geometry of the cyclononenone moiety. The 1H‐ and 13C‐NMR spectra showed that the unsaturated nine‐membered ring of (E)‐isomer 3 in C6D6 and (D6)acetone solution exists in a sole conformation of type B1, which is similar to its solid‐state conformation. The (Z)‐isomer 2 in C6D6, CDCl3, and (D6)acetone solution, however, exists in two conformational forms of different families, with different orientation of the carbonyl group, the predominant form (85%) corresponding to the conformation of type A1 and the minor (15%) to the conformation A2 present also in the crystalline state. In this solid‐state conformations of the nine‐membered ring of both compounds, the 19‐Me and 5‐oxo groups are ‘β’‐oriented. The NMR analysis suggests that the nine‐membered ring of 4 has a conformation o...f type C1 in CDCl3 solution.

Keywords:
Conformations / X‐ray crystallographic analysis / NMR / Steroids
Source:
Helvetica Chimica Acta, 2005, 88, 10, 2812-2821
Publisher:
  • Wiley

DOI: 10.1002/hlca.200590221

ISSN: 0018-019X; 1522-2675

WoS: 000233154200025

Scopus: 2-s2.0-27644454700
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URI
https://cer.ihtm.bg.ac.rs/handle/123456789/4186
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