CAS: 16930-96-4; Hexyl (E)-2-Methylbut-2-Enoate

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142-90-5 32360-05-7 2495-27-4

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(2E)-Hexenyl Tiglate

📜(2E)-Hexenyl Tiglate置于rhcl(Pph3)3 氢气体系中,用 苯 用作溶剂,20.0 °C,101.32 Kpa 条件下,反应 15.0H,以93%的收率获得(E)-2-甲基-2-丁烯酸己酯
参考文献:Total Syntheses Of Ipomoeassin B And E
标题:Total Syntheses Of Ipomoeassin B And E
摘要:A Concise,Flexible,And Efficient Total Synthesis Of The Cytotoxic Resin Glycosides Ipomoeassin B (1) And Ipomoeassin E (2) Is Reported Which Features The Advantages Of A Novel Protecting Group Strategy Employing (Z)-3-Dimethyl(Phenyl)Silyl-2-Propenoic Acid As Cinnamic Acid Surrogate. The Use Of This Readily Available Compound Allowed The Macrocycle Of The Glycolipids To Be Formed By Ring Closing Olefin Metathesis (Rcm) With The Aid Of The Second Generation Grubbs Carbene Complex 12. The Resulting E/z Mixture Could Be Selectively Hydrogenated Using Wilkinson'S Catalyst [rhcl(Pph3)(3)] Without Affecting The Unsaturated Esters In The Periphery Of The Compound,Before The C-Silyl Group Was Cleaved Off With Tasf [tris(Dimethylamino)Sulfonium Difluorotrimethylsilicate] Under Notably Mild Conditions To Release The Required Cinnamate Moiety. Other Key Steps Of The Synthesis Route Comprise The Formation Of The Disaccharide Linkage By The Trichloroacetimidate Method,The Formation Of The Chiral Acid Segment 19 Via A Vo(Acac)(2)-Catalyzed,Tert-Buooh-Induced Oxidative Rearrangement Of The Optically Pure Furyl Alcohol (-)-15 (Achmatowicz-Type Reaction),And A Reductive Cleavage Of The 4,6-O-P-Methoxybenzylidene Acetal In 5 With Nabh3Cn And Me3Sicl (Tmscl),The Regiochemical Course Of Which Was Found To Be Opposite To That Previously Reported In The Literature For Sterically Less Encumbered Substrates.
Doi:10.1021/ja068901G