CAS: 3650-17-7; (+)-Hirsutic Acid

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(-)-Complicatic Acid 51741-93-6

📜Methyl (1S,2Ar,2Br,2Cr,4S,5Ar,5Bs,5Cs)-1-(Benzoyloxy)-Decahydro-4,5B-Dimethyl-2-Oxo-1H-Cyclopenta[a]Cyclopropa[cd]Pentalene-4-Carboxylate置于aluminum Oxide,Sodium Hydroxide,Sodium Tetrahydroborate,Samarium Diiodide,双氧水,对甲苯磺酸,Lithium Iodide,Lithium Hexamethyldisilazane,2-碘酰基苯甲酸体系中,用 四氢呋喃,甲醇,乙醚,乙醇,二氯甲烷,水,二甲基亚砜,N,N-二甲基甲酰胺,甲苯 用作溶剂,化学反应 128.25H,反应生成(1Ar-(1Aalpha,2Beta,3Abeta,3Balpha,5Alpha,6Aalpha,7As*))-十氢-2-羟基-3A,5-二甲基-3-亚甲基-环戊二烯并(4,5)二并环戊烯并(1,6A-B)环氧乙烯-5-羧酸
参考文献:Chemoenzymatic Total Syntheses Of The Linear Triquinane-Type Natural Products (+)-Hirsutic Acid And (−)-Complicatic Acid From Toluene
标题:Chemoenzymatic Total Syntheses Of The Linear Triquinane-Type Natural Products (+)-Hirsutic Acid And (−)-Complicatic Acid From Toluene
摘要:Total Syntheses Of Title Natural Products,1 And 2,Have Been Achieved Using The Cis-1,2-Dihydrocatechol 7 As Starting Material. Compound 7 Is Readily Obtained In Large Quantity And Enantiomerically Pure Form Through The Whole-Cell Biotransformation Of Toluene Using The Genetically Engineered Micro-Organism Escherichia Coli Jm109 (Pdtg601) That Over-Expresses The Enzyme Toluene Dioxygenase (Tdo). Three Key Chemical Steps Were Employed In These Syntheses,The First Of Which Was A High-Pressure-Promoted Diels-Alder Cycloaddition Reaction Between Diene 8 And Cyclopentenone To Give Adduct 9. The Second Key Step Was The Photochemically Promoted Oxa-Di-Pi-Methane Rearrangement Of The Bicyclo[2.2.2] octenone Derivative,18,Of 9 To Give 20 While The Third Key Step Was The Reductive Cleavage Of The Last Compound So As To Afford The Linear Triquinane 22. Elaboration Of Compound 22 To Targets 1 And 2 Followed Conventional And/or Established Procedures. Single-Crystal X-Ray Analyses Were Carried Out On Compounds 10-13,15,18,24,And 34. (C) 2007 Elsevier Ltd. All Rights Reserved.
Doi:10.1016/j.Tet.2007.03.073