(R)-6-((1E,3E,7E,9E)-10-((1S,2S)-2-methylcyclopropyl)deca-1,3,7,9-tet raen-1-yl)-5,6-dihydro-2H-pyran-2-one | 1386388-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (R)-6-((1E,3E,7E,9E)-10-((1S,2S)-2-methylcyclopropyl)deca-1,3,7,9-tet raen-1-yl)-5,6-dihydro-2H-pyran-2-one
• 英文别名: coibacin A；(2R)-2-[(1E,3E,7E,9E)-10-[(1S,2S)-2-methylcyclopropyl]deca-1,3,7,9-tetraenyl]-2,3-dihydropyran-6-one
• CAS: 1386388-83-5
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: DUZRSWWIBKKPQI-KEMYCKAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (R)-6-formyl-2-isopropyloxy-5,6-dihydro-2H-pyran 在 manganese(IV) oxide 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 pyridinium chlorochromate 、 calcium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 81.17h， 生成 (R)-6-((1E,3E,7E,9E)-10-((1S,2S)-2-methylcyclopropyl)deca-1,3,7,9-tet raen-1-yl)-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Coibacins A and B: Total Synthesis and Stereochemical Revision

  摘要：

  The interface between synthetic organic chemistry and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent anti-inflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Additionally, we synthesized coibacin B on the basis of the assignment of configuration for coibacin A.

  DOI：

  10.1021/jo402339y

文献信息

• Coibacins A and B: Total Synthesis and Stereochemical Revision
  作者：Vânia M. T. Carneiro、Carolina M. Avila、Marcy J. Balunas、William H. Gerwick、Ronaldo A. Pilli

  DOI：10.1021/jo402339y

  日期：2014.1.17

  The interface between synthetic organic chemistry and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent anti-inflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Additionally, we synthesized coibacin B on the basis of the assignment of configuration for coibacin A.