4-epi-clonostachydiol | 887195-59-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 4-epi-clonostachydiol
• 英文别名: (3E,5R,6R,9E,11R,14R)-5,11-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione；epi-clonostachydiol
• CAS: 887195-59-7
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: SSVNIYICRYPPEB-FROFMIMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-epi-clonostachydiol 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以40%的产率得到[(2R,3R,4E,8R,11R,12E)-2,8-dimethyl-6,14-dioxo-3-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxy-1,7-dioxacyclotetradeca-4,12-dien-11-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  4-酮-Clonostachydiol的不对称总合成和绝对构型的修订

  摘要：

  14元天然大环双内酯4-酮-clonostachydiol及其对映体的第一次总合成已分13个步骤完成，总收率分别为8.4％和8.0％。4-酮-氯水苏糖醇1的绝对构型已被修改为（5 S，10 S，13 S）。

  DOI：

  10.1021/jo900370a
• 作为产物：
  描述：

  (3E,5R,6R,9E,11R,14R)-11-(benzyloxy)-5-(4-methoxybenzyloxy)-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以78%的产率得到4-epi-clonostachydiol
  参考文献：
  名称：

  Studies directed toward the first total synthesis of acremodiol and acremonol

  摘要：

  Studies directed toward the synthesis of acremodiol and acremonol resulted in the synthesis of two macrodiolides 1, la, and 2 besides 3. The attempted synthesis of 1 and 2 confirmed that the absolute stereochemistry defined in the earlier report is incorrect. Compound I was synthesized by RCM-mediated macrocyclization. Attempted synthesis of 2 failed to give good yields in the cyclization, and la and 2 were synthesized by the Yamaguchi macrolactonization method. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.030

文献信息

• Bioactivity Profiling Using HPLC/Microtiter-Plate Analysis:  Application to a New Zealand Marine Alga-Derived Fungus, <i>Gliocladium</i> sp.
  作者：Gerhard Lang、Maya I. Mitova、Gill Ellis、Sonia van der Sar、Richard K. Phipps、John W. Blunt、Nicholas J. Cummings、Anthony L. J. Cole、Murray H. G. Munro

  DOI：10.1021/np0504917

  日期：2006.4.1

  HPLC/microtiter-plate-based generation of activity profiles the extract of a marine alga-derived fungus, identified as Gliocladium sp., was shown to contain the known strongly cytotoxic metabolite 4-keto-clonostachydiol (1) and also clonostachydiol (2) as well as gliotide (3), a new cyclodepsipeptide containing several D-amino acids. The absolute configuration of 1 was elucidated by reduction to 2,

  使用基于HPLC /微量滴定板的活性谱图生成方法，鉴定为Gliocladium sp。的海藻衍生真菌提取物含有已知的强细胞毒性代谢物4-酮-clonostachydiol（1）以及clonostachydiol（2） ）和格列肽（3），这是一种新的含有两个D-氨基酸的环二肽。通过还原为2来阐明1的绝对构型，并制备了氯氧水苏糖醇的另外两种氧化衍生物（5、6），并对其生物学活性进行了评估。
• Studies directed toward the first total synthesis of acremodiol and acremonol
  作者：Gangavaram V.M. Sharma、Samala Mallesham、Chirutha Chandra Mouli

  DOI：10.1016/j.tetasy.2009.10.030

  日期：2009.11

  Studies directed toward the synthesis of acremodiol and acremonol resulted in the synthesis of two macrodiolides 1, la, and 2 besides 3. The attempted synthesis of 1 and 2 confirmed that the absolute stereochemistry defined in the earlier report is incorrect. Compound I was synthesized by RCM-mediated macrocyclization. Attempted synthesis of 2 failed to give good yields in the cyclization, and la and 2 were synthesized by the Yamaguchi macrolactonization method. (C) 2009 Elsevier Ltd. All rights reserved.
• Asymmetric Total Synthesis and Revision of the Absolute Configuration of 4-Keto-Clonostachydiol
  作者：Junjie Han、Yingpeng Su、Tuo Jiang、Yanfen Xu、Xing Huo、Xuegong She、Xinfu Pan

  DOI：10.1021/jo900370a

  日期：2009.5.15

  The first total synthesis of the 14-membered natural macrocyclic bislactone 4-keto-clonostachydiol, along with its enantiomer, has been accomplished in 13 steps with overall yields of 8.4% and 8.0%, respectively. The absolute configuration of 4-keto-clonostachydiol 1 has been revised as (5S,10S,13S).

  14元天然大环双内酯4-酮-clonostachydiol及其对映体的第一次总合成已分13个步骤完成，总收率分别为8.4％和8.0％。4-酮-氯水苏糖醇1的绝对构型已被修改为（5 S，10 S，13 S）。