Synthesis of a Nitro Analogue of Plakoric Acid  

作　　者：张琦 金红霞 刘鹤华 伍贻康 

机构地区：[1]State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

出　　处：《Chinese Journal of Chemistry》2006年第9期1190-1195,共6页中国化学（英文版）

基　　金：Project supported by the National Natural Science Foundation of China （Nos. 20025207, 20272071, 20372075, 20321202） and the Chinese Academy of Sciences （No. KGCX2-SW-209）. Dedicated to Professor Xikui Jiang on the occasion of his 80th birthday.

摘　　要：Synthesis of a nitro analogue of plakoric acid is presented. The peroxy bond was incorporated into the substrate structure through a boron trifluoride etherate catalyzed methoxy-hydroperoxy group partial exchange reaction in diethyl ether with urea-hydrogen peroxide complex （UHP, a commercially available solid reagent） as the source of the hydrogen peroxide. Under the given conditions, only one of the two methoxyl groups underwent the MeO—— OOH exchange and the resulting hydroperoxy hemiketal proceeded directly to the end product through an intramolecular Michael addition of the hydroperoxyl group to the nitro group activated carbon-carbon double bond.Synthesis of a nitro analogue of plakoric acid is presented. The peroxy bond was incorporated into the substrate structure through a boron trifluoride etherate catalyzed methoxy-hydroperoxy group partial exchange reaction in diethyl ether with urea-hydrogen peroxide complex （UHP, a commercially available solid reagent） as the source of the hydrogen peroxide. Under the given conditions, only one of the two methoxyl groups underwent the MeO—— OOH exchange and the resulting hydroperoxy hemiketal proceeded directly to the end product through an intramolecular Michael addition of the hydroperoxyl group to the nitro group activated carbon-carbon double bond.

关 键 词：PEROXIDE CYCLIZATION hemiketal EXCHANGE ANTIMALARIAL 

分 类 号：R978.61[医药卫生—药品]