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

Li-Ming      Zhao; De-Feng      Xu; Wen      Zhou; Shao-Shun      Li

doi:10.2174/157017808783955899

Abstract

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.

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

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Letters in Organic Chemistry

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

Volume: 5 Issue: 3

Author(s): Li-Ming Zhao, De-Feng Xu, Wen Zhou and Shao-Shun Li

Affiliation:

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

Abstract: 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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Zhao Li-Ming, Xu De-Feng, Zhou Wen and Li Shao-Shun, Concise Formal Synthesis of (±)-Shikonin Via a Highly α-Regioselective Prenylation of 1, 4, 5, 8-Tetramethoxynaphthalene-2-Carbaldehyde, Letters in Organic Chemistry 2008; 5 (3) . https://dx.doi.org/10.2174/157017808783955899