📜(3-Acetyloxy-2-Ethoxycarbonylbenzyl)-Triphenylphosphonium Bromide置于palladium On Activated Charcoal 吡啶,氢氧化钾,氢气,Sodium Ethanolate,三氟乙酸体系中,用 乙醇,二氯甲烷,乙酸乙酯 用作溶剂,化学反应 29.88H,反应生成白花前胡甲素
参考文献:Enantiodifferentiation In Taste Perception Of The Phyllodulcins
标题:Enantiodifferentiation In Taste Perception Of The Phyllodulcins
摘要:Both Enantiomers Of Phyllodulcin 1 Have Been Prepared. Ester 2 Was Synthesized In A Wittig Reaction From O-Benzyl Isovanillin. The Corresponding Stilbene Carboxylic Acid 3 Could Be Cyclized With Cf3Co2H To Produce The 3'-Benzyl Ether 4 Of (+/-)-Phyllodulcin. Acylation With (1R,4S)-Camphanoyl Chloride Gave First 5 And After Hydrogenolysis Of The Benzyl Ether Group In 5 The Diastereomeric Esters 6. The Diastereomerically Pure 8-(1R,4S)-Camphanoate (+)-6 Of (R)-Phyllodulcin Could Be Isolated By Repeated Recrystallization. With (1S,4R)-Camphanoyl Chloride The Enantiomeric 8-(1S,4R)-Camphanoate (-)-6 Of O-Phyllodulcin Could Be Prepared Via Ent-5 From A Mixture Of The Diastereomeric Esters Ent-6. Ethanolysis Of (+)-6 Gave (R)-Phyllodulcin [(+)-1] With 99% Ee. The Enantiomeric (S)-(-)-1 With 98% Ee Could Be Obtained From (-)-6. While (+)-1,The Enantiomer occuring In Fermented Leaves Of Amacha,Has An Intense Sweet Taste,The Enantiomer (-)-1 Is Completely Tasteless.
Doi:10.1016/0957-4166(95)00367-X