Abstract
A synthesis of the BC ring moiety of brachialactone, a fusicoccane-type diterpene isolated from the tropical forage grass Brachiaria humidicola and found to inhibit nitrification by soil microbes, is described. Several precursors including the C ring were synthesized from a known chiral cyclopentane, and then subjected to the conditions for the Mizoroki-Heck reaction. Substrates incorporating vinyl (R = H) or enone (R = COCH3) moieties and incorporating an S configuration at C-2 successfully underwent intramolecular Mizoroki-Heck reaction, giving the BC ring structure of brachialactone.
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