New 1-alk(en)yl-1,3,5-trihydroxycyclohexanes from the Dufour gland of the African ant Crematogaster nigriceps

[en] The Dufour gland of the African ant Crematogaster nigriceps contains a mixture of at least eight 1-heptadec(en)yl- and 1-nonadec(en)yl-1,3,5-trihydroxycyclohexane derivatives, the mono-unsaturated components being the major ones (about 65%). They are accompanied by small amounts of (Z,Z)-dienic derivatives (<10%). The structures, the relative and absolute configurations, and the preferred conformation of these new compounds have been established by spectroscopic and chemical methods, whereas the positions of the double bond in the alkenyl chains were determined by DMDS derivatisation followed by linked scan EIMS.

Disciplines :

Chemistry

Author, co-author :

Laurent, Pascal ; Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle

Hamdani, Anissa

Braekman, Jean-Claude

Daloze, Désiré

Isbell, Lynne

De Biseau, Jean-Christophe

Pasteels, Jacques

Language :

English

Title :

New 1-alk(en)yl-1,3,5-trihydroxycyclohexanes from the Dufour gland of the African ant Crematogaster nigriceps

Publication date :

2003

Journal title :

Tetrahedron Letters

ISSN :

0040-4039

Publisher :

Elsevier, Oxford, United Kingdom

Volume :

Issue :

Pages :

1383-1386

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 04 June 2010

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Bibliography

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Δδ=δS-δR: OH-1: +0.06; H-2ax: 0; H-2eq: -0.01; H-3eq: -0.02; OH-3: -0.15; H-4ax: -0.11; H-4eq: -0.06; H-5ax: 0; H-6ax: +0.11; H-6eq: +0.05; H2C-1′: +0.01 and +0.02.
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