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Issue 7, 2001
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Synthesis and NMR characterisation of novel highly cyclised polyprenoid hydrocarbons from sediments

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Abstract

We report here on the identification of two novel hexacyclic alkanes (C33 and C35) occurring in bitumen. The C35 compound 1 was identified by comparison with a standard obtained by synthesis involving a biomimetic proton-induced extensive cyclisation of an acyclic heptaprenoid. This cascade cyclisation allows the formation of eleven asymmetric centres present in the natural compound in only one step. The C33 analogue 2 was identified by NMR studies after isolation from the saturated hydrocarbon fraction of a bituminous rock. Both compounds are “orphan” molecular fossils of biological lipids of unknown origin formed by the extensive cyclisation of higher regular polyprenoids.

Graphical abstract: Synthesis and NMR characterisation of novel highly cyclised polyprenoid hydrocarbons from sediments

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Article information


Submitted
06 Oct 2000
Accepted
01 Feb 2001
First published
07 Mar 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 711-719
Article type
Paper

Synthesis and NMR characterisation of novel highly cyclised polyprenoid hydrocarbons from sediments

E. Grosjean, J. Poinsot, A. Charrié-Duhaut, S. Tabuteau, P. Adam, J. Trendel, P. Schaeffer, J. Connan, D. Dessort and P. Albrecht, J. Chem. Soc., Perkin Trans. 1, 2001, 711
DOI: 10.1039/B008104N

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