Synthesis and NMR characterisation of novel highly cyclised polyprenoidhydrocarbons from sediments
2001
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.
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