litseaverticillol D

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: litseaverticillol D
• 英文别名: (4S,5R)-4-hydroxy-5-[(1E,4E)-6-hydroxy-2,6-dimethylhepta-1,4-dienyl]-2-methylcyclopent-2-en-1-one
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: BYCYEWSQFFBUSU-AYJMRYRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 litseaverticillol D 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 5-[(1E,4E)-2,6-dimethyl-6-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-hepta-1,4-dienyl]-3-methyl-4-oxo-cyclopent-2-enyl ester
  参考文献：
  名称：

  Natural anti-HIV agents. Part 3: Litseaverticillols A–H, novel sesquiterpenes from Litsea verticillata

  摘要：

  Bioassay directed-fractionation led to the identification of litseaverticillols A-H (1-8) from the leaves and twigs of Litsea verticillata Hance. These new sesquiterpenes possess a unique skeleton that was recently designated as 'litseane'. The structures of these compounds were determined by spectroscopic means including I D and 2D NMR data. Structural configurations were determined by ROESY experiments. Mosher ester reactions and optical rotation measurements established the sesquiterpenes 1-8 as racemates. Isolates 1-8 inhibited HIV-1 replication in HOG.R5 cells with IC50 values ranging from 2 to 15 mug/ml (8-58 muM) while affecting the growth of HOG.R5 at concentrations 2-3-fold higher. Based on this data, structure-activity relationships can be discerned, suggesting compounds of this class are good candidates for analog production. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01491-6
• 作为产物：
  描述：

  (+/-)-1α-hydroxy-(E)-litse-2,6,10-trien-4-one 在 氧气 、 亚甲兰 、 三苯基膦 作用下， 以 氯仿 为溶剂， 反应 0.11h， 以35%的产率得到litseaverticillol D
  参考文献：
  名称：

  拟南芥A，C，D，F和G的仿生全合成：单线态氧引发的级联反应。

  摘要：

  DOI：

  10.1002/anie.200352180

文献信息

• Illustrating the Power of Singlet Oxygen Chemistry in a Synthetic Context: Biomimetic Syntheses of Litseaverticillols A-G, I and J and the Structural Reassignment of Litseaverticillol E
  作者：Georgios Vassilikogiannakis、Ioannis Margaros、Tamsyn Montagnon、Manolis Stratakis

  DOI：10.1002/chem.200401311

  日期：2005.10.7

  Biomimetic syntheses of the litseaverticillols A-G, I and J are reported herein. The syntheses rely heavily on the application of two different modes of reaction for photochemically generated singlet oxygen, namely, the [4+2] cycloaddition of singlet oxygen (1O2) with furans and the ene reaction of 1O2 with double bonds. The highlight of these syntheses is a one-pot cascade sequence, involving five

  本文报道了枯草麻木AG，I和J的仿生合成。合成很大程度上依赖于光化学生成的单线态氧的两种不同反应模式的应用，即单线态氧（1O2）与呋喃的[4 + 2]环加成反应和1O2与双键的烯反应。这些合成的亮点是一锅级联序列，涉及由[4 + 2]反应引发的五种合成操作，以形成功能齐全的联苯并香茅醇核心。然后使用一系列的区域选择性烯反应适当地官能化侧链。邻苯二酚E的合成（包括最初提出的结构和实际结构）都可以对该天然产物进行结构上的重新分配。
• Biomimetic Total Synthesis of Litseaverticillols A, C, D, F, and G: Singlet-Oxygen-Initiated Cascades
  作者：Georgios Vassilikogiannakis、Manolis Stratakis

  DOI：10.1002/anie.200352180

  日期：2003.11.17
• Natural anti-HIV agents. Part 3: Litseaverticillols A–H, novel sesquiterpenes from Litsea verticillata
  作者：Hong-Jie Zhang、Ghee Teng Tan、Vu Dinh Hoang、Nguyen Van Hung、Nguyen Manh Cuong、Djaja Doel Soejarto、John M Pezzuto、Harry H.S Fong

  DOI：10.1016/s0040-4020(02)01491-6

  日期：2003.1

  Bioassay directed-fractionation led to the identification of litseaverticillols A-H (1-8) from the leaves and twigs of Litsea verticillata Hance. These new sesquiterpenes possess a unique skeleton that was recently designated as 'litseane'. The structures of these compounds were determined by spectroscopic means including I D and 2D NMR data. Structural configurations were determined by ROESY experiments. Mosher ester reactions and optical rotation measurements established the sesquiterpenes 1-8 as racemates. Isolates 1-8 inhibited HIV-1 replication in HOG.R5 cells with IC50 values ranging from 2 to 15 mug/ml (8-58 muM) while affecting the growth of HOG.R5 at concentrations 2-3-fold higher. Based on this data, structure-activity relationships can be discerned, suggesting compounds of this class are good candidates for analog production. (C) 2002 Elsevier Science Ltd. All rights reserved.