A formal total synthesis of the marine sesquiterpene (±)-9- isocyanoneopupukeanane starting from the readily available monoterpene carvone has been accomplished employing a combination of intermolecular Michael addition-intramolecular Michael addition reaction and an intramolecular rhodium carbenoid C-H insertion reaction as key steps, and identifying the isopropenyl group as a masked hydroxy group. © 2005 Elsevier Ltd. All rights reserved.