Synthesis and Conformational Analysis of New 17-Alkyl Derivatives of Lupanine and Their Perchlorate Salts

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Title:Synthesis and Conformational Analysis of New 17-Alkyl Derivatives of Lupanine and Their Perchlorate Salts
Creators:
Jasiewicz, Beata
Boczoń, Władysław
Kurek, Joanna
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 11, pp. 2068-2080
Uncontrolled Keywords:Grignard reaction, IR spectroscopy, Alkyl substituents, Lupanine derivatives, Tertiary amines, Bisquinolizidine alkaloids, NMR spectroscopy

Abstract

New 17-alkyl derivatives of lupanine and their perchlorate salts have been synthesised. Substituents at C-17 are introduced by treatment of C(17)=N(16) immonium perchlorate <strong>2</strong> with alkylmagnesium compounds. NMR spectra of the new compounds have been taken to study the chemical shift changes caused by the introduced alkyl substituents, ethyl and butyl. In 17-alkyl derivatives (17-ethyl- (<strong>3</strong>) and 17-butyllupanine (<strong>4</strong>)) the substituent is equatorially oriented. All the lupanine derivatives analysed have the same structure, i.e. ring C in a boat conformation. The reaction of 17-butyllupanine (<strong>4</strong>) and 17-cyanolupanine (<strong>5</strong>) with methyllithium has led to 17-butyl-2-methyl-2,3-didehydrosparteine (<strong>6</strong>), 17-butyl-2-methylsparteine (<strong>7</strong>) and 17-cyano-2-methyl-2,3-didehydrosparteine (<strong>8</strong>). <p>

Title:Synthesis and Conformational Analysis of New 17-Alkyl Derivatives of Lupanine and Their Perchlorate Salts
Creators:
Jasiewicz, Beata
Boczoń, Władysław
Kurek, Joanna
Uncontrolled Keywords:Grignard reaction, IR spectroscopy, Alkyl substituents, Lupanine derivatives, Tertiary amines, Bisquinolizidine alkaloids, 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:69
Number:11
Page Range:pp. 2068-2080
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20042068UNSPECIFIED
ID Code:2321
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Jasiewicz, Beata; Boczoń, Władysław; Kurek, Joanna (2004) Synthesis and Conformational Analysis of New 17-Alkyl Derivatives of Lupanine and Their Perchlorate Salts. Collection of Czechoslovak Chemical Communications, 69 (11). pp. 2068-2080. ISSN 0010-0765

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