(1R,3R,6E,9R,12E,14R)-3,9-dimethyl-4,10,15,17-tetraoxabicyclo[12.3.0]heptadeca-6,12-diene-5,11,16-trione | 485323-95-3

• 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: (1R,3R,6E,9R,12E,14R)-3,9-dimethyl-4,10,15,17-tetraoxabicyclo[12.3.0]heptadeca-6,12-diene-5,11,16-trione
• CAS: 485323-95-3
• 化学式: C₁₅H₁₈O₇
• 分子量: 310.304
• InChiKey: DAFDZSZMMQLFSR-RSNJVVJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,3R,6E,9R,12E,14R)-3,9-dimethyl-4,10,15,17-tetraoxabicyclo[12.3.0]heptadeca-6,12-diene-5,11,16-trione 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 甲酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (-)-(6R,14R,12S,3E,9E)-6,14-dimethyl-12-hydroxy-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione 、 cis-colletol
  参考文献：
  名称：

  Enantioselective Syntheses of Colletodiol, Colletol, and Grahamimycin A

  摘要：

  [GRAPHICS]The enantioselective synthesis of colletodiol has been achieved in 11 steps from methyl 1,3,5-octatrienoate and 16 total steps from both ethyl sorbate and methyl 1,3,5-octatrienoate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a 5-hydroxy-1-enoate and an 7-hydroxy-1,3-dienoate. These esters were further functionalized, coupled, and macrolactonized to provide colletodiol after deprotection. Grahamimycin A and colletol were synthesized in one and two steps, respectively, from colletodiol.

  DOI：

  10.1021/ol0269502
• 作为产物：
  描述：

  methyl (E)-3-[(4R,5R)-5-[(2R)-2-hydroxypropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate 在 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 Dowex 50W-8H⁽¹⁺⁾ resin 、 trichlorobenzoyl chloride 、 四丁基氟化铵 、 4-(dimethylamino)pyridine hydrochloride 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 78.0h， 生成 (1R,3R,6E,9R,12E,14R)-3,9-dimethyl-4,10,15,17-tetraoxabicyclo[12.3.0]heptadeca-6,12-diene-5,11,16-trione
  参考文献：
  名称：

  Enantioselective Syntheses of Colletodiol, Colletol, and Grahamimycin A

  摘要：

  [GRAPHICS]The enantioselective synthesis of colletodiol has been achieved in 11 steps from methyl 1,3,5-octatrienoate and 16 total steps from both ethyl sorbate and methyl 1,3,5-octatrienoate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a 5-hydroxy-1-enoate and an 7-hydroxy-1,3-dienoate. These esters were further functionalized, coupled, and macrolactonized to provide colletodiol after deprotection. Grahamimycin A and colletol were synthesized in one and two steps, respectively, from colletodiol.

  DOI：

  10.1021/ol0269502

文献信息

• Enantioselective Syntheses of Colletodiol, Colletol, and Grahamimycin A
  作者：Thomas J. Hunter、George A. O'Doherty

  DOI：10.1021/ol0269502

  日期：2002.12.1

  [GRAPHICS]The enantioselective synthesis of colletodiol has been achieved in 11 steps from methyl 1,3,5-octatrienoate and 16 total steps from both ethyl sorbate and methyl 1,3,5-octatrienoate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a 5-hydroxy-1-enoate and an 7-hydroxy-1,3-dienoate. These esters were further functionalized, coupled, and macrolactonized to provide colletodiol after deprotection. Grahamimycin A and colletol were synthesized in one and two steps, respectively, from colletodiol.