CAS: 35825-57-1; (R)-1,2,6,7,8,9-Hexahydro-1,6,6-Trimethyl-Phenanthro(1,2-B)Furan-10,11-Dione

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CAS号109664-02-0 新隐丹参酮 | CAS号2270-59-9 5-溴-2-甲基-2-戊烯 | CAS号578-57-4 邻溴苯甲醚 | CAS号171979-69-4 1,1-dimethyl-5-... | CAS号33214-70-9 5-methoxy-1,1-d... | CAS号100-66-3 苯甲醚 | CAS号171979-70-7 1-(1'-methoxyph... | CAS号171979-68-3 1-(5,5-dimethyl... | CAS号171979-67-2 2-diazo-1-(5,5-... | CAS号109664-02-0 新隐丹参酮 | CAS号568-72-9 丹参酮IIA

📜3-((S)-1-((Tert-Butyldimethylsilyl)Oxy)-2-Propyl)-7,7-Dimethyl-4-Hydroxy-2-((Triisopropylsilyl)Oxy)-7,8,9,10-Tetrahydrophenanthrene置于硫酸,四丁基氟化铵,氧气体系中,用 四氢呋喃,乙醇 用作溶剂,化学反应 40.75H,反应生成隐丹参酮
参考文献:Aromatic Annulation Strategy For The Synthesis Of Angularly-Fused Diterpenoid Quinones. Total Synthesis Of (+)-Neocryptotanshinone,(-)-Cryptotanshinone,Tanshinone Iia,And (.+-.)-Royleanone
标题:Aromatic Annulation Strategy For The Synthesis Of Angularly-Fused Diterpenoid Quinones. Total Synthesis Of (+)-Neocryptotanshinone,(-)-Cryptotanshinone,Tanshinone Iia,And (.+-.)-Royleanone
摘要:The Application Of A Photochemical Aromatic Annulation Strategy In Highly Efficient Total Syntheses Of Several Diterpenoid Quinones Isolated From The Traditional Chinese Medicine Dan Shen Is Reported. The Pivotal Step In Each Synthesis Involves The Assembly Of A Key Tricyclic Intermediate Via The Application Of A Recently Developed ''Second-Generation'' Photochemical Aromatic Annulation Method For The Construction Of Highly Substituted Aromatic Systems. In The Total Synthesis Of Neocrypto-Tanshinone,;The Synthesis Of The Requisite Diazo Ketone Annulation Substrate 7 Was Achieved Using Palladium-Mediated Coupling Reactions And An Intramolecular Friedel-Crafts Cyclization To Form Key Carbon-Carbon Bonds. The Pivotal Aromatic Annulation Reaction Was Then Accomplished By Irradiating A Solution Of The Diazo Ketone 7 And The Readily Available Siloxyalkyne 6 In Benzene At Room Temperature. The Desired Tricyclic Phenol 16 Was Produced In 58-65% Yield And Was Then Converted To (+)-Neocryptotanshinone (1) By Treatment With Tetra-N-Butylammonium Fluoride In The Presence Of Oxygen. Cyclization To Generate (-)-Cryptotanshinone (2) Was Accomplished In High Yield By Brief Exposure Of 1 To An Ethanolic Solution Of Concentrated Sulfuric Acid,And Dehydrogenation Of 2 With Ddq Furnished Tanshinone Iia (3). As A Further Demonstration Of The Utility Of The Photochemical Aromatic Annulation Strategy In The Construction Of Angularly-Fused Diterpenes,The Total Synthesis Of(+/-)-Royleanone (4) Was Also Investigated. Irradiation Of A Solution Of The Diazo Ketone 18 And Siloxyalkyne 25 Produced The Tricyclic Intermediate 26,Which Was Converted In Two Steps To Royleanone By Desilylation And Oxidation.
Doi:10.1021/jo00131A006

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