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Compound 3, representing the tetracyclic core structure of CP-225,917, was prepared from bridgehead olefin 9, which was first converted into ketone 13. Peterson olefination then gave 15, and this was elaborated into the anhydride 19, from which crystalline 3 was reached by a sequence of deprotection and oxidation steps.
Compound 1, representing the core structure of CP-225,917, including the anhydride subunit, was prepared by an approach involving siloxy-Cope rearrangement of the strained lactone 18, in which C(15) of the anhydride is already present. The C(14) carbon was introduced at a later stage with the Tebbe reagent. Further elaboration gave homoallylic alcohol 25, which was converted into epoxy aldehyde 27,...
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