Catalytic, asymmetric transannular aldolizations: total synthesis of (+)-hirsutene
Carley L Chandler1, Benjamin List
1Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim an der Ruhr, Germany.
Abstract:
We report an asymmetric, catalytic transannular aldolization that provides polycyclic products useful for natural product synthesis. We found that a proline-derivative catalyzes the transannular aldol reaction of 1,4-cyclooctanediones to the corresponding cyclic beta-hydroxy ketones in good yields and with high enantioselectivities. The utility of our reaction has been demonstrated in a total synthesis of (+)-hirustene.
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