CAS: 142950-86-5; (4As,10As)-7-Isopropyl-1,4A-Dimethyl-5,8-Dioxo-3,4,4A,5,8,9,10,10A-Octahydrophenanthrene-2-Carboxylic Acid

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(+)-(4aS,10aR)-5,8-Dimethoxy-1,4a-dimethyl-7-isopropyl-3,4,4a,9,10,10a-hexahydrophenanthrene-2-carboxylic acid 4-bromo-2-isopropyl-phenol 2-isopropyl-6-methoxy-1-naphthol 4-Bromo-2-isopropyl-6-methoxy-1-naphthol

📜4-溴-2-异丙基苯酚置于palladium Diacetate 1,1'-双(二苯基膦)二茂铁,氢氧化钾,Sodium Hydroxide,Sodium Chlorite,Copper(L) Iodide,草酰氯,Ammonium Cerium(Iv) Nitrate,三正丁胺,Dimethyl Sulfide Borane,氨基磺酸,氨,甲基锂,双氧水,Lithium,Potassium Carbonate,对甲苯磺酸,二甲基亚砜,三乙胺,叔丁醇体系中,用 1,4-二氧六环,甲醇,乙醚,水,N,N-二甲基甲酰胺,丙酮,乙腈,苯 用作溶剂,化学反应 130.21H,反应生成吡嗪,三甲基[(甲硫基)甲基]-(9Ci)
参考文献:Synthetic Studies On Diterpenoid Quinones With Interleukin-1 Inhibitory Activity. Total Synthesis Of (.+-.)-And (+)-Triptoquinone A
标题:Synthetic Studies On Diterpenoid Quinones With Interleukin-1 Inhibitory Activity. Total Synthesis Of (.+-.)-And (+)-Triptoquinone A
摘要:An Efficient First Total Synthesis Of (+/-)-And (+)-Triptoquinone A (1),A Novel Diterpenoid Quinone With Significant Inhibitory Activity Against Interleukin-1 Releases,Has Been Completed. Birch Reduction Of Tricyclic Enone (+/-)-7,Prepared From Known 6-Methoxy-2-Isopropyl-1-Naphthol (22),Which Is Readily Available In Large Quantities,Was Followed By Immediate Enolate Trapping To Provide Silyl Enol Ether (+/-)-30. Compound 30 Was Converted Into Carboxylic Acid (+/-)-4 Via The Corresponding Enol Triflate (+/-)-31 Either By Sequential Palladium-Catalyzed Carbonylation And Oxidation Or By Direct Carboxylation. The Total Synthesis Of (+/-)-1 Was Completed By Oxidation Of (+/-)-4 With Can In 12 Steps From 22 In 19% Overall Yield At Best. A Second,Enantioselective Total Synthesis Of (+)-1 Was Accomplished Via (+/-)-7,Which Was Prepared By (-)-N-[4-(Trifluoromethyl)Benzyl]Cinchonidinium Bromide (33) Catalyzed Asymmetric Michael Reaction Of 6 With Ethyl Vinyl Ketone And A Subsequent Aldol Condensation. The Absolute Structures Of Triptoquinone B (2) And C (3),Which Were Isolated Concomitantly With Triptoquinone A From The Same Plant Sources,Were Established By A Series Of Chemical Reactions Based On (+)-7.
Doi:10.1021/jo00081A021