| 1402589-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1402589-23-4
• 化学式: C₄₄H₄₃NO₁₁
• 分子量: 761.826
• InChiKey: AMRAWUVDNCBCBZ-XBXSULLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.65
• 重原子数：
  56.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  175.52
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  2,2-二甲基-1,3-丙二醇 在 4-二甲氨基吡啶 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 二氯苯酚溴酯 、 四丁基氟化铵 、 titanium(IV)isopropoxide 、 caesium carbonate 、 戴斯-马丁氧化剂 、 (1R)-反-N,N′-1,2-环己二基双(1,1,1-三氟甲磺酰胺) 、 臭氧 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 4-氯-3-硝基苯甲酸 、 zinc(II) iodide 、 (S)-(-)-5,5-二氯-6,6-二甲氧基-2,2-双(二苯基磷酸)-1,1-联苯基 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 109.34h， 生成 、
  参考文献：
  名称：

  Studies toward the Unique Pederin Family Member Psymberin: Full Structure Elucidation, Two Alternative Total Syntheses, and Analogs

  摘要：

  Two synthetic approaches to psymberin have been accomplished. A highly convergent first generation synthesis led to the complete stereochemical assignment and demonstrated that psymberin and irciniastatin A are identical compounds. This synthesis featured a diastereoselective aldol coupling between the aryl fragment and a central tetrahydropyran core and a novel one-pot procedure to convert an amide, via intermediacy of a sensitive methyl imidate, to the N-acyl aminal reminiscent of psymberin. The highlights of the second generation synthesis include an efficient iridium-catalyzed enantioselective bisallylation of neopentyl glycol and a stepwise Sonogashira coupling/cycloisomerization/reduction sequence to construct the dihydroisocoumarin unit. The two synthetic avenues were achieved in 17-18 steps (longest linear sequence, similar to 14-15 isolations) from 3 fragments prepared in 7-8 (first generation) and 3-8 (second generation) steps each. This convergent approach allowed for the preparation of sufficient amounts of psymberin (similar to 0.5 g) for follow-up biological studies. Meanwhile, our highly flexible strategy enabled the design and synthesis of multiple analogs, including a psymberin pederin hybrid, termed psympederin, that proved crucial to a comprehensive understanding of the chemical biology of psymberin and related compounds that will be described in a subsequent manuscript.

  DOI：

  10.1021/ja3057612