Chapmans (O. L. Chapman, then at Iowa State, later UCLA)

Chapter 24, Problem 24.36

(choose chapter or problem)

Chapmans (O. L. Chapman, then at Iowa State, later UCLA) classic total synthesis of (6)-Carpanone is so remarkably simple that it is used as an undergraduate laboratory preparation. It is modeled on a possible biosynthetic route for this lignan-derived natural product. Phenol oxidations fi gure prominently in many such biosyntheses of natural products. In one step, this reaction creates no less than fi ve contiguous chiral centers, all in the correct relative confi guration. K+tert-BuO DMSO ()- Carpanone O OH O O O O O OH [O] O O O O O O O O O O H H (a) Give a mechanism for the fi rst step of the reaction and explain why it goes in the direction it does. (b) The oxidation step uses a palladium salt. Suggest a mechanism for this coupling, which you have not encountered. (Hint: Do not concern yourself with the role of the metal except as an acceptor of electrons.) (c) The third step is spontaneous. Give a mechanism for this reaction and show how it accounts for the stereochemistry of the fi nal product. (d) Would you expect the product to be racemic or a single enantiomer?

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