Organic Letters 2001-12-27

Application of Lewis acid catalyzed tropone [6+4] cycloadditions to the synthesis of the core of CP-225,917.

L Isakovic, J A Ashenhurst, J L Gleason

Index: Org. Lett. 3(26) , 4189-92, (2001)

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Abstract

The carbocyclic core of CP-225,917 and CP-263,114 is accessible through the [6+4] cycloaddition of a tropone with a 2-substituted cyclopentadiene. Examination of this reaction has revealed for the first time that this cycloaddition process is catalyzed by Lewis acids, including lanthanide triflates. Cycloadditions of several mono-, di-, and trisubstituted tropones with 2-silyloxycyclopentadienes using ZnCl(2) catalysis are found to proceed in good yield and, in many cases, with excellent diastereoselectivity. Subsequent transformation to the core of the CP-molecules involves a site-selective Baeyer-Villiger oxidation of a tricyclic diketone, followed by a syn-elimination process. [reaction: see text]