Total synthesis of mucocin

The synthesis of the potent antitumor agent, mucocin, 1, was efficiently achieved in 20 steps from cyclododecatriene, thus confirming the proposed structure of this unusual member of the Annonaceous acetogenins. Demonstrating the power of the "naked" carbon skeleton strategy, all seven asymmetric centers in the key fragment of the molecule were introduced by double AE reaction followed by double AD reaction. Simultaneous two ring closure reactions provided both the THP and THF rings in a single step.