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Experimental

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Molecule 43 was the product of a Simmons-Smith cyclopropanation reaction on 41 through intermediate 42. During formation of the cyclopropane ring, the methoxymethyl protecting group was converted into a methoxyethyl group via the insertion of a CH2. Compound 43 was reacted with pyridinium chlorochromate (PCC) in dichloromethane at room temperature and the methoxyethyl group (OMOE) was removed under these conditions, allowing the two alcohol groups to be oxidized into the bis-ketone intermediate 44. Compound 44 was then dissolved in acetic acid. The cyclopropane ring of 44 was then reductively cleaved to form two methyl groups using hydrogen gas (H2), platinum oxide (PtO2) to produce compound 45.