Synthesis and Conformational Analysis of Disubstituted Sparteine Derivatives

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Title:Synthesis and Conformational Analysis of Disubstituted Sparteine Derivatives
Creators:
Boczoń, Władysław
Jasiewicz, Beata
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 68, 4, pp. 696-710
Uncontrolled Keywords:Bis-quinolizidine alkaloids, Tertiary amines, Chiral saturated heterocycles, Sparteine derivatives, IR spectroscopy, NMR spectroscopy

Abstract

Synthesis of disubstituted sparteine derivatives and their diperchlorate salts was performed. Their IR and NMR spectra were analysed to determine the structure of these compounds, as well as the substituent and the protonation effects. It was shown that both unsaturated (2,17β-dimethyl-2,3-didehydrosparteine (<strong>12</strong>), 17β-isopropyl-2-methyl-2,3-didehydrosparteine (<strong>13</strong>)) and saturated (2,17β-dimethylsparteine (<strong>14</strong>), 17β-isopropyl-2-methylsparteine (<strong>15</strong>)) newly obtained sparteine derivatives have the same configurational-conformational system: <i>trans</i> A/B chair/chair, <i>trans</i> C/D boat/chair. The methyl and the isopropyl (both equatorial) groups at C-17 appear the elements stabilizing the boat-chair system of the C/D rings, which does not change either on the introduction of the second substituent to the opposite quinolizidine system (the A/B rings) or on protonation. The protonation of the free bases obtained gives only disalts. The atoms undergoing the protonation are either C-3 and N-16 in <strong>12</strong> and <strong>13</strong> or both nitrogen atoms (N-1 and N-16) in <strong>14</strong> and <strong>15</strong>. The methyl group introduced on the carbon atom C-2 takes equatorial position, as in 2-methylsparteine (<strong>2</strong>). <p>

Title:Synthesis and Conformational Analysis of Disubstituted Sparteine Derivatives
Creators:
Boczoń, Władysław
Jasiewicz, Beata
Uncontrolled Keywords:Bis-quinolizidine alkaloids, Tertiary amines, Chiral saturated heterocycles, Sparteine derivatives, IR spectroscopy, NMR spectroscopy
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:68
Number:4
Page Range:pp. 696-710
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20030696UNSPECIFIED
ID Code:2079
Item Type:Article
Deposited On:06 Feb 2009 17:15
Last Modified:06 Feb 2009 16:15

Citation

Boczoń, Władysław; Jasiewicz, Beata (2003) Synthesis and Conformational Analysis of Disubstituted Sparteine Derivatives. Collection of Czechoslovak Chemical Communications, 68 (4). pp. 696-710. ISSN 0010-0765

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