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Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

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

Volume 5 , Issue 3 , 2008

Page: [234 - 236] Pages: 3

DOI: 10.2174/157017808783955899

Price: $65


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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