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Concise Formal Synthesis of (±)-Shikonin Via a Highly α-Regioselective Prenylation of 1, 4, 5, 8-Tetramethoxynaphthalene-2-Carbaldehyde

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A concise formal synthesis of (±)-shikonin via a highly α-regioselective prenylation is achieved. The novelty of the procedure lies in the introduction of side chain of shikonin in one step via prenylation of 1, 4, 5, 8- tetramethoxynaphthalene-2-carbaldehyde under mild conditions without producing any γ-isomer.

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Keywords: Shikonin; oxonia-cope rearrangement; prenylation; regioselectivity; synthesis

Document Type: Research Article

Publication date: 2008-04-01

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