(9R,10S)-8-deshydroxyajudazol A | 1412889-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (9R,10S)-8-deshydroxyajudazol A
• 英文别名: (E)-N-[(2E,6Z,8Z)-11-[4-[(2S)-2-[(3R)-8-hydroxy-7-methyl-1-oxo-3,4-dihydroisochromen-3-yl]propyl]-1,3-oxazol-2-yl]dodeca-2,6,8,11-tetraenyl]-3-methoxy-N-methylbut-2-enamide
• CAS: 1412889-76-9
• 化学式: C₃₄H₄₂N₂O₆
• 分子量: 574.717
• InChiKey: RTNHGMHEBRKVDU-HRLFELJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (Z)-6-碘-5-己烯-1-醇 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 四溴化碳 、 copper(II) acetate monohydrate 、 二异丁基氢化铝 、 1-羟基苯并三唑 、 silver nitrate 、 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide methiodide 、 三乙胺 、 三苯基膦 、 pyridinium chlorochromate 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 99.0h， 生成 (9R,10S)-8-deshydroxyajudazol A
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure of 8-Deshydroxyajudazol A: A Modified Approach to 2,4-Disubstituted Oxazoles

  摘要：

  The total synthesis of the proposed structure for the minor Myxobacterial metabolite 8-deshydroxyajudazol A (3) is described. The isochromanone moiety present in the eastern fragment was constructed by an intramolecular-Diels-Alder (IMDA). Difficulties were encountered with the formation of the 2,4-disubstituted oxazole, so this was synthesized via a modified approach. This involved selective acylation of the diol 7 with acid 8, azide displacement of the secondary alcohol, and subsequent azide reduction in the presence of base which induced an O,N shift to give the hydroxyamide 23. Cyclodehydration then gave the desired oxazole 24 and deprotection followed by mesylation and elimination produced the C15 alkene S. Sonogashira coupling with the eastern fragment vinyl iodide 6 and partial reduction yielded 8-deshydroxyajudazol A (3).

  DOI：

  10.1021/jo302055w

文献信息

• Total Synthesis of the Proposed Structure of 8-Deshydroxyajudazol A: A Modified Approach to 2,4-Disubstituted Oxazoles
  作者：Stephen Birkett、Danny Ganame、Bill C. Hawkins、Sébastien Meiries、Tim Quach、Mark A. Rizzacasa

  DOI：10.1021/jo302055w

  日期：2013.1.4

  The total synthesis of the proposed structure for the minor Myxobacterial metabolite 8-deshydroxyajudazol A (3) is described. The isochromanone moiety present in the eastern fragment was constructed by an intramolecular-Diels-Alder (IMDA). Difficulties were encountered with the formation of the 2,4-disubstituted oxazole, so this was synthesized via a modified approach. This involved selective acylation of the diol 7 with acid 8, azide displacement of the secondary alcohol, and subsequent azide reduction in the presence of base which induced an O,N shift to give the hydroxyamide 23. Cyclodehydration then gave the desired oxazole 24 and deprotection followed by mesylation and elimination produced the C15 alkene S. Sonogashira coupling with the eastern fragment vinyl iodide 6 and partial reduction yielded 8-deshydroxyajudazol A (3).