(-)-preussochromone D | 1359030-30-0

• 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: (-)-preussochromone D
• 英文别名: Preussochromone D；methyl (1R,2R,3S,3aR,9aR)-1,2,8-trihydroxy-3-methyl-9-oxo-2,3,3a,9a-tetrahydrocyclopenta[b]chromene-1-carboxylate
• CAS: 1359030-30-0
• 化学式: C₁₅H₁₆O₇
• 分子量: 308.288
• InChiKey: FHOZFIROEVROQO-BIBPAEJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-preussochromone D 、 甲氧基-三氟甲基苯 以 pyridine-d₅ 为溶剂， 反应 12.0h， 以0.8 mg的产率得到methyl (1R,2R,3R,3aR,9aR)-1,8-dihydroxy-3-methyl-9-oxo-2-[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxy-2,3,3a,9a-tetrahydrocyclopenta[b]chromene-1-carboxylate
  参考文献：
  名称：

  A Thiopyranchromenone and Other Chromone Derivatives from an Endolichenic Fungus, Preussia africana

  摘要：

  The first example of a naturally occurring thiopyranchromenone, preussochromone A (1), and five other new chromone derivatives, preussochromones B-F (2-6), were isolated from solid cultures of an endolichenic fungus, Preussia africana. The structures of 1-6 were established primarily by NMR experiments, and 2 and 4 were further confirmed by X-ray crystallography. The absolute configurations of 1 and 2 were determined by the application of electronic circular dichroism (ECD), whereas those of C-5 in 3, C-6 in 4, and the 6,7-diol in 5 were deduced via the CD data of the in situ formed [Rh-2(OCOCF3)(4)] complex, the modified Mosher method, and Snatzke's method, respectively. Compounds 1 and 3 showed significant cytotoxicity against A549 cells.

  DOI：

  10.1021/np2009362
• 作为产物：
  描述：

  5-羟基色满-4-酮 在 盐酸 、 硼烷四氢呋喃络合物 、 草酰氯 、 2,6-二叔丁基-4-甲基苯酚 、 (S)-N-Ts-para-benzyloxy phenylglycine 、 双氧水 、 diethylzinc 、 二异丁基氢化铝 、 caesium carbonate 、 二甲基亚砜 、 sodium hydroxide 、 scandium tris(trifluoromethanesulfonate) 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 正庚烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 14.66h， 生成 (-)-preussochromone D
  参考文献：
  名称：

  （-）-Preussochromone D的全合成

  摘要：

  报道了天然产物（-）-前异色酮D的高效，立体选择性的合成。通过将苯并二氢吡喃酮非对映选择性分子内羟醛加成到α-酮酸酯中来组装三环骨架。进一步的关键步骤是二异丙烯基锌不对称地将1，4-加成至色酮和将重氮乙酸甲酯的分子间非对映选择性羟醛加成至醛。重氮基被氧化生成α-酮酸酯，同时通过使用二氟甲基醚作为保护基团可以防止在苯并二氢吡喃酮上发生氧化副反应。

  DOI：

  10.1021/acs.orglett.9b01594

文献信息

• Second Generation Total Synthesis of (–)‐Preussochromone D
  作者：Eric Kerste、Marc Paul Beller、Ulrich Koert

  DOI：10.1002/ejoc.202000465

  日期：2020.6.30

  acetals to chromenone‐based substrates on multigram‐scale has been achieved. The introduced conjugate addition shortens the total synthesis of (–)‐preussochromone D and establishes a robust entry for further investigations towards the total synthesis of preussochromone E and F.

  达到了立体选择性，高收率的甲基甲硅烷基乙烯酮缩醛在多克级的基于苯醌的底物上的添加。引入的共轭物加成缩短了（-）-前异色酮D的总合成，并为进一步研究前异色酮E和F的总合成奠定了坚实的基础。
• Total Synthesis of (−)-Preussochromone D
  作者：Eric Kerste、Klaus Harms、Ulrich Koert

  DOI：10.1021/acs.orglett.9b01594

  日期：2019.6.7

  An efficient, stereoselective synthesis of the natural product (−)-preussochromone D is reported. The tricyclic skeleton was assembled by a diastereoselective intramolecular aldol addition of a chromanone to an α-ketoester. Further key steps are an asymmetric 1,4-addition of diisopropenyl zinc to a chromenone and an intermolecular diastereoselective aldol addition of methyl diazoacetate to an aldehyde

  报道了天然产物（-）-前异色酮D的高效，立体选择性的合成。通过将苯并二氢吡喃酮非对映选择性分子内羟醛加成到α-酮酸酯中来组装三环骨架。进一步的关键步骤是二异丙烯基锌不对称地将1，4-加成至色酮和将重氮乙酸甲酯的分子间非对映选择性羟醛加成至醛。重氮基被氧化生成α-酮酸酯，同时通过使用二氟甲基醚作为保护基团可以防止在苯并二氢吡喃酮上发生氧化副反应。
• A Thiopyranchromenone and Other Chromone Derivatives from an Endolichenic Fungus, <i>Preussia africana</i>
  作者：Fan Zhang、Li Li、Shubin Niu、Yikang Si、Liangdong Guo、Xuejun Jiang、Yongsheng Che

  DOI：10.1021/np2009362

  日期：2012.2.24

  The first example of a naturally occurring thiopyranchromenone, preussochromone A (1), and five other new chromone derivatives, preussochromones B-F (2-6), were isolated from solid cultures of an endolichenic fungus, Preussia africana. The structures of 1-6 were established primarily by NMR experiments, and 2 and 4 were further confirmed by X-ray crystallography. The absolute configurations of 1 and 2 were determined by the application of electronic circular dichroism (ECD), whereas those of C-5 in 3, C-6 in 4, and the 6,7-diol in 5 were deduced via the CD data of the in situ formed [Rh-2(OCOCF3)(4)] complex, the modified Mosher method, and Snatzke's method, respectively. Compounds 1 and 3 showed significant cytotoxicity against A549 cells.