2-nitro-N-(triisopropylsilyloxy)benzenesulfonamide | 1384122-95-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-nitro-N-(triisopropylsilyloxy)benzenesulfonamide
• CAS: 1384122-95-5
• 化学式: C₁₅H₂₆N₂O₅SSi
• 分子量: 374.533
• InChiKey: QZTOYHJHXACFJD-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  (4bSR,8aSR)-2-ethoxy-4b-(3-iodopropyl)-3,4,4b,6,7,8,8a,9-octahydro-2H-1-oxafluoren-5-one 、 2-nitro-N-(triisopropylsilyloxy)benzenesulfonamide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以91%的产率得到(4bSR,8aSR)-2-ethoxy-4b-((3-triisopropylsilyoxy-2-nitrobenzenesulfonyl)aminopropyl)-3,4,4b,6,7,8,8a,9-octahydro-2H-1-oxafluoren-5-one
  参考文献：
  名称：

  Total Synthesis of (+)-Sieboldine A: Evolution of a Pinacol-Terminated Cyclization Strategy

  摘要：

  This article describes synthetic studies that culminated in the first total synthesis of the Lycopodium alkaloid sieboldine A. During this study, a number of pinacol-terminated cationic cyclizations were examined to form the cis-hydrindanone core of sieboldine A. Of these, a mild Au(I)-promoted 1,6-enyne cyclization that was terminated by a semipinacol rearrangement proved to be most efficient. Fashioning the unprecedented N-hydroxyazacyclononane ring embedded within the bicyclo[5.2.1]decane-N,O-acetal moiety of sieboldine A was a formidable challenge. Ultimately, the enantioselective total synthesis of (+)-sieboldine A was completed by forming this ring in good yield by cyclization of a protected-hydroxylamine thioglycoside precursor.

  DOI：

  10.1021/jo300872y