Citation: De Feng XU, Xiao Juan GUO, Zhao Hui XU, Shao Shun LI. A Novel Total Synthesis of (±)Shikonin[J]. Chinese Chemical Letters, ;2006, 17(7): 871-873. shu

A Novel Total Synthesis of (±)Shikonin

School of Pharmacy, Shanghai Jiaotong University, Shanghai 200030

Received Date: 21 October 2005

Fund Project: This project was supported by Shanghai-SK Research and Development Foundation (2003014h).

A novel total synthesis of (±)shikonin 1 was presented. The key intermediate 6 was achieved by the formylation of 1,8:4,5-bis(methylenedioxy)naphthalene 5 with N-methylforma-nilide in good yield. It was first reported that the addition of prenyllithium to 2-formyl-1,8:4,5-bismethylenedioxy naphthalene 6 gave 2-(1-hydroxy-4-methylpentyl) 1,8:4,5-bis(methylenedioxy)naphthalene 8 in 45% yield and 2-(1-hydroxy-2,2-dimethyl-3-butenyl)-1,8:4,5-bis(methylene-dioxy)naphthalene 9 in 48% yield. After the electrooxide deprotection of 8, (±)shikonin 1 was prepared in high yield.
- (±)Shikonin,
- total synthesis,
- prenyllithium
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