CAS: 12771-72-1; (5R,10S,10Ar,14As,15Bs)-10,10A-Dihydroxy-7-Methoxy-2,2-Dimethyl-5-(2-Methylprop-1-En-1-yl)-1,10,10A,12,13,14,14A,15B-Octahydro-5H,15H-3,4-Dioxa-5A,11A,15A-Triazacycloocta[lm]Indeno[5,6-B]Fluorene-11,15(2H)-Dione

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CAS号111139-38-9 Fumitremorgin B

📜N-[叔丁氧羰基]-L-色氨酸甲酯置于n-甲基吗啉,盐酸,四氧化锇,1,10-菲罗啉,(1,5-Cyclooctadiene)(Methoxy)Iridium(I) Dimer,三氟化硼乙醚,四丁基氟化铵,氯化锆(Iv),碳酸氢钠,溶剂黄146,二乙胺,亚硝基苯,三氟乙酸,联硼酸频那醇酯,频那醇硼烷,Lithium Hexamethyldisilazane体系中,用 四氢呋喃,正己烷,二氯甲烷,氯仿,水,乙酸乙酯,1,2-二氯乙烷,N,N-二甲基甲酰胺,丙酮,乙腈,叔丁醇 用作溶剂,化学反应 107.42H,反应生成疣孢青霉原
参考文献:Total Synthesis Of Verruculogen And Fumitremorgin A Enabled By Ligand-Controlled C-h Borylation
标题:Total Synthesis Of Verruculogen And Fumitremorgin A Enabled By Ligand-Controlled C-h Borylation
摘要:Verruculogen And Fumitremorgin A Are Bioactive Alkaloids That Contain A Unique Eight-Membered Endoperoxide. Although Related Natural Products Such As Fumitremorgins B And C Have Been Previously Synthesized,We Report The First Synthesis Of The More Complex,Endoperoxide-Containing Members Of This Family. A Concise Route To Verruculogen And Fumitremorgin A Relied Not Only On A Hydroperoxide/indole Hemiaminal Cyclization,But Also On The Ability To Access The Seemingly Simple Starting Material,6-Methoxytryptophan. An Iridium-Catalyzed C-H Borylation/chan-Lam Procedure Guided By An N-Tips Group Enabled The Conversion Of A Tryptophan Derivative Into A 6-Methoxytryptophan Derivative,Proving To Be A General Way To Functionalize The C6 Position Of An N,C3-Disubstituted Indole For The Synthesis Of Indole-Containing Natural Products And Pharmaceuticals.
Doi:10.1021/jacs.5B07154