11-deoxyblennolide D | 1571891-63-8

• 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: 11-deoxyblennolide D
• 英文别名: 11-Deoxyblennolide D；methyl (2S)-5-hydroxy-2-[(2S,3S)-3-methyl-5-oxooxolan-2-yl]-4-oxo-3H-chromene-2-carboxylate
• CAS: 1571891-63-8
• 化学式: C₁₆H₁₆O₇
• 分子量: 320.299
• InChiKey: QOBIDOOHIOXPIA-QZOJXLDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl (S)-5-methoxy-2-[(2S,3S)-3-methyl-5-oxotetrahydrofuran-2-yl]chroman-2-carboxylate 在 potassium permanganate 、 三溴化硼 、 magnesium sulfate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 10.5h， 生成 11-deoxyblennolide D
  参考文献：
  名称：

  The Paecilin Puzzle ‒ Enantioselective Synthesis of the Proposed Structures of Paecilin A and B

  摘要：

  For the synthesis of the two diastereomers 3c and 3d of the proposed structure of paecilin B (3) phenol 19, containing an alkenyl moiety, was treated with Pd(II) in the presence of the chiral BOXAX ligand 9b to give 20 with 96% ee. A subsequent Sharpless dihydroxylation afforded two isomeric diols, which were further transfoimed into 31 and 32. The final steps included removal of the silyl protecting group with simultaneous lactone formation, oxidation and cleavage of the methyl ether. For the preparation of the dimeric paecilin A (1) brominated intermediate 38 was treated with (Bpin)(2), S-Phos and Pd(OAc)(2). The spectroscopic data of the new compounds did not match those of the isolated natural products.

  DOI：

  10.3987/com-13-s(s)68

文献信息

• The Paecilin Puzzle ‒ Enantioselective Synthesis of the Proposed Structures of Paecilin A and B
  作者：Lutz F. Tietze、Ling Ma、Stefan Jackenkroll、Johannes R. Reiner、Judith Hierold、Boopathy Gnanaprakasam、Sven Heidemann

  DOI：10.3987/com-13-s(s)68

  日期：——

  For the synthesis of the two diastereomers 3c and 3d of the proposed structure of paecilin B (3) phenol 19, containing an alkenyl moiety, was treated with Pd(II) in the presence of the chiral BOXAX ligand 9b to give 20 with 96% ee. A subsequent Sharpless dihydroxylation afforded two isomeric diols, which were further transfoimed into 31 and 32. The final steps included removal of the silyl protecting group with simultaneous lactone formation, oxidation and cleavage of the methyl ether. For the preparation of the dimeric paecilin A (1) brominated intermediate 38 was treated with (Bpin)(2), S-Phos and Pd(OAc)(2). The spectroscopic data of the new compounds did not match those of the isolated natural products.