7,11-cyclobotryococca-5,12,26-triene, a novel botryococcene-related hydrocarbon occurring in natural environments

Org Lett. 2000 May 4;2(9):1271-4. doi: 10.1021/ol0056980.


[formula: see text] With the unambiguous structural characterization of 7,11-cyclobotryococca-5,12,26-triene 1 by NMR, a novel C30 botryococcene-related hydrocarbon skeleton bearing a midchain five-membered ring has been identified in organic-rich sediments from Lake Cadagno (Switzerland). This compound may originate from the green alga Botryococcus braunii (race B) widespread in recent and past environments. Alternatively, it may also be a yet unreported lipid of green sulfur photosynthetic bacteria (Chlorobiaceae) or a microbial transformation product of the farnesol produced by the latter.