Abstract
The odoriferous principle of black tea has been produced from 2,2-dimethylcyclopentanone. The reaction sequence begins with 1,2-addition of 5-lithio-2-methyl-2,3-dihydrofuran to this ketone and immediate acid-catalyzed ring expansion of the resulting carbinols to a separable pair of spiro ethers. Individual conversion of these diastereomers to α,β-unsaturated ketones is followed by tandem condensation with the methyllithium−lithium bromide complex and oxidation with pyridinium chlorochromate.
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