(+/-)-lycoposerramine T

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-lycoposerramine T
• 英文别名: [(1S,2S,4S,6S,9E)-4-acetyloxy-4-methyl-8-oxo-13-azatricyclo[7.7.0.01,6]hexadec-9-en-2-yl] acetate
• 化学式: C₂₀H₂₉NO₅
• 分子量: 363.454
• InChiKey: RHNSVLZNRRBSJZ-UMRMIEEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2,2-三氟乙基甲酸酯 、 (+/-)-lycoposerramine T 以 甲基叔丁基醚 为溶剂， 反应 2.5h， 以52%的产率得到N-formyllycoposerramine-T
  参考文献：
  名称：

  一种新的石松生物碱，Lycoposerramine-R，具有新颖骨架和三新Fawcettimine相关生物碱蛇足石松

  摘要：

  Abstractmagnified imageA new Lycopodium alkaloid, lycoposerramine‐R, possessing an unusual tetracyclic ring system, was isolated from Lycopodium serratum. Its structure as well as those of three new co‐existing fawcettimine‐related alkaloids were elucidated by means of extensive spectroscopic analysis.

  DOI：

  10.1002/hlca.200800327
• 作为产物：
  描述：

  2-(3-(benzyloxy)prop-1-yn-1-yl)cyclopent-2-en-1-one 在 bismuth(lll) trifluoromethanesulfonate 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 bis(2-methoxyethyl) azodicarboxylate 、 manganese(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 indium 、 bis(acetylacetonate)oxovanadium 、 10 wt% Pd(OH)2 on carbon 、 四丁基氟化铵 、 水 、 氢气 、 碳酸氢钠 、 potassium carbonate 、 caesium carbonate 、 对甲苯磺酸 、 苯硫酚 、 三乙胺 、 N,N-二异丙基乙胺 、 9-硼双环[3.3.1]壬烷 、 间氯过氧苯甲酸 、 三苯基膦 、 氢化铝 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 癸烷 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 、 甲苯 、 乙腈 为溶剂， 反应 103.83h， 生成 (+/-)-lycoposerramine T
  参考文献：
  名称：

  Syntheses of (±)-Serratine, (±)-Lycoposerramine T, and (±)-Lycopoclavamine B

  摘要：

  The first total syntheses of (+/-)-serratine, (+/-)-lycoposerramine T, and (+/-)-lycopoclavamine B have been accomplished. The functionalized octahydroindane skeleton of these natural products was constructed by an efficient Diels-Alder reaction of an alpha-alkynylcyclopentenone and the stereoselective introduction of a tertiary hydroxyl group. Two of these natural products were divergently synthesized from the same synthetic intermediate at a later stage.

  DOI：

  10.1021/ol400628h

文献信息

• Syntheses of (±)-Serratine, (±)-Lycoposerramine T, and (±)-Lycopoclavamine B
  作者：Hisaaki Zaimoku、Hiroshi Nishide、Asami Nishibata、Naoya Goto、Tsuyoshi Taniguchi、Hiroyuki Ishibashi

  DOI：10.1021/ol400628h

  日期：2013.5.3

  The first total syntheses of (+/-)-serratine, (+/-)-lycoposerramine T, and (+/-)-lycopoclavamine B have been accomplished. The functionalized octahydroindane skeleton of these natural products was constructed by an efficient Diels-Alder reaction of an alpha-alkynylcyclopentenone and the stereoselective introduction of a tertiary hydroxyl group. Two of these natural products were divergently synthesized from the same synthetic intermediate at a later stage.
• A New<i>Lycopodium</i>Alkaloid, Lycoposerramine-R, with a Novel Skeleton and Three New Fawcettimine-Related Alkaloids from<i>Lycopodium serratum</i>
  作者：Kazuaki Katakawa、Noriyuki Kogure、Mariko Kitajima、Hiromitsu Takayama

  DOI：10.1002/hlca.200800327

  日期：2009.3

  Abstractmagnified imageA new Lycopodium alkaloid, lycoposerramine‐R, possessing an unusual tetracyclic ring system, was isolated from Lycopodium serratum. Its structure as well as those of three new co‐existing fawcettimine‐related alkaloids were elucidated by means of extensive spectroscopic analysis.