(6R,12R,14R)-(3E,9E)-12-hydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8,11-trione | 50376-39-1

• 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: (6R,12R,14R)-(3E,9E)-12-hydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8,11-trione
• 英文别名: 6R,12R,14R-colletoketol；grahamimycin A；colletoketol；(3E,6R,9E,12R,14R)-12-hydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8,11-trione
• CAS: 50376-39-1
• 化学式: C₁₄H₁₈O₆
• 分子量: 282.293
• InChiKey: CZZDNDKEYUQSIO-WLENGAGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (6R,12R,14R)-(3E,9E)-12-hydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8,11-trione 在 sodium tetrahydroborate 、 二甲基亚砜 、 三乙胺 、 对甲苯磺酰氯 作用下， 生成 (R,R)-(-)-Grahamimycin A₁
  参考文献：
  名称：

  Biosynthesis of collectodiol and related polyketide macrodiolides in Cytospora sp. ATTCC 20502: synthesis and metabolism of advanced intermediates

  摘要：

  三烯 3 和 6 已被专门标记并掺入大二内酯（macrodiolide）中，colletodio 1 已在 Cytospora sp 培养物中得到证实。 ATCC 20502；仿生反应的结果表明，colleketol 2 和 grahamimycin A17 都可以在单一氧化步骤中由collectodiol 生物合成。

  DOI：

  10.1039/c39930000738
• 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 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 lithium hydroxide 、 Dowex 50W-8H⁽¹⁺⁾ resin 、 trichlorobenzoyl chloride 、 四丁基氟化铵 、 4-(dimethylamino)pyridine hydrochloride 、 对甲苯磺酸 、 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 82.0h， 生成 (6R,12R,14R)-(3E,9E)-12-hydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8,11-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

• First Total Synthesis of Grahamimycin A
  作者：Yuichi Kobayashi、Michitaka Matsuumi

  DOI：10.1021/jo000762c

  日期：2000.10.1
• Hoeller, Ulrich; Koenig, Gabriele M.; Wright, Anthony D., European Journal of Organic Chemistry, 1999, # 11, p. 2949 - 2955
  作者：Hoeller, Ulrich、Koenig, Gabriele M.、Wright, Anthony D.

  DOI：——

  日期：——
• 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.
• Biosynthesis of collectodiol and related polyketide macrodiolides in Cytospora sp. ATTCC 20502: synthesis and metabolism of advanced intermediates
  作者：John A. O'Neill、Thomas J. Simpson、Christine L. Willis

  DOI：10.1039/c39930000738

  日期：——

  The triene 3 and 6 have been syntesised in specifically labeled from and their incorporation into the macrodiolide, colletodio 1 demonstrated in cultures of Cytospora sp. ATCC 20502; results of a biomimetic reaction indicate that both colletoketol 2 and grahamimycin A17 may be biosynthesized in a single oxidation step from collectodiol.

  三烯 3 和 6 已被专门标记并掺入大二内酯（macrodiolide）中，colletodio 1 已在 Cytospora sp 培养物中得到证实。 ATCC 20502；仿生反应的结果表明，colleketol 2 和 grahamimycin A17 都可以在单一氧化步骤中由collectodiol 生物合成。