15-epilatrunculin A | 127852-20-4

• 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: 15-epilatrunculin A
• 英文别名: Epilatrunculin A；(4R)-4-[(1S,4Z,8E,10Z,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-1,3-thiazolidin-2-one
• CAS: 127852-20-4
• 化学式: C₂₂H₃₁NO₅S
• 分子量: 421.558
• InChiKey: DDVBPZROPPMBLW-BDOXQPRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (2Z,6E,8Z)-(S)-12-[(2R,4R,6R)-4-Hydroxy-6-methoxy-6-((R)-2-oxo-thiazolidin-4-yl)-tetrahydro-pyran-2-yl]-3,10-dimethyl-dodeca-2,6,8-trienoic acid 2-trimethylsilanyl-ethyl ester 在 四丁基氟化铵 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 水 、 二甲基亚砜 、 苯 为溶剂， 反应 2.0h， 生成 15-epilatrunculin A
  参考文献：
  名称：

  White, James D.; Kawasaki, Motoji, Journal of the American Chemical Society, 1990, vol. 112, # 12, p. 4991 - 4993

  摘要：

  DOI：

文献信息

• Total synthesis of (+)-latrunculin A, an ichthyotoxic metabolite of the sponge Latrunculia magnifica and its C-15 epimer
  作者：James D. White、Motoji Kawasaki

  DOI：10.1021/jo00046a008

  日期：1992.9

  Latrunculin A (1), an ichthyotoxic metabolite of the sponge Latrunculia magnifica with potent inhibitory action on microfilament-mediated processes involved in cell division, was synthesized via a convergent approach. Construction of a major segment of the latrunculin backbone was accomplished by means of a three-component coupling of aldehyde 24, beta-keto ester 27, and phosphonium salt 26, which established the conjugated EZ-diene moiety of 31. The thiazolidinone subunit of 1 was elaborated in the form of 39 from L-cysteine and was linked to 35 without nitrogen protection. Final lactonization of 47 was carried out using the Mitsunobu protocol. A parallel sequence employing the epimeric seco acid 48 produced 15-epilatrunculin A.