(6R,9S)-penicillenol A1 | 1039041-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6R,9S)-penicillenol A1
• 英文别名: Penicillenol A₁；(3Z,5S)-5-[(1R)-1-hydroxyethyl]-3-[(2S)-1-hydroxy-2-methyloctylidene]-1-methylpyrrolidine-2,4-dione
• CAS: 1039041-76-3
• 化学式: C₁₆H₂₇NO₄
• 分子量: 297.395
• InChiKey: KWUIFAHSOVLDLQ-IMQZKJBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6R,9S)-penicillenol A1 在 4-二甲氨基吡啶 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 生成 (5Z,2'S)-5-ethylidene-3-(1-hydroxy-2-methyloct-1-ylidene)-1-methylpyrrolidine-2,4-dione 、 (5E,2'S)-5-ethylidene-3-(1-hydroxy-2-methyloct-1-ylidene)-1-methylpyrrolidine-2,4-dione
  参考文献：
  名称：

  Synthesis, stereochemical assignment, and bioactivity of the Penicillium metabolites penicillenols B1 and B2

  摘要：

  The Penicillium metabolites penicillenols B-1 and B-2 were synthesised for the first time by elimination of a mesylated penicillenol A precursor as obtained from an L-threonine derived tetramic acid. The (Z,S)-and (E,S)-configured diastereomers were identical to the natural compounds as to NMR spectra and optical rotations. Both isomers showed antiproliferative effects against cancer and endothelial cell lines and penicillenol B-1 was also notably antibiotic against Staphylococcus aureus. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.116
• 作为产物：
  描述：

  9H-fluoren-9-ylmethyl (4S)-4-[(1R)-1-acetyloxyethyl]-5-oxo-1,3-oxazolidine-3-carboxylate 在 哌啶 、 吡啶 、 盐酸 、 三乙基硅烷 、 4-二甲氨基吡啶 、 aluminum (III) chloride 、 palladium on activated charcoal 、 氢氟酸 、 氢气 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 60.0 ℃ 、100.0 kPa 条件下， 反应 92.17h， 生成 (6R,9S)-penicillenol A1
  参考文献：
  名称：

  Synthesis, stereochemical assignment, and bioactivity of the Penicillium metabolites penicillenols B1 and B2

  摘要：

  The Penicillium metabolites penicillenols B-1 and B-2 were synthesised for the first time by elimination of a mesylated penicillenol A precursor as obtained from an L-threonine derived tetramic acid. The (Z,S)-and (E,S)-configured diastereomers were identical to the natural compounds as to NMR spectra and optical rotations. Both isomers showed antiproliferative effects against cancer and endothelial cell lines and penicillenol B-1 was also notably antibiotic against Staphylococcus aureus. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.116

文献信息

• First Stereoselective Synthesis of Penicillenol A1 via Novel O- to C-Acyl Rearrangement of O-Acyltetramic Acid
  作者：Hidemi Yoda、Tetsuya Sengoku、Jolanta Wierzejska、Masaki Takahashi

  DOI：10.1055/s-0030-1259045

  日期：2010.12

  The first stereoselective synthesis of penicillenol A1 has been accomplished in nine steps from l-threonine. The 3-acyltetramic acid core of penicillenol A1 was constructed by successful O- to C-acyl rearrangement.

  通过九个步骤，首次以 l-苏氨酸为原料立体选择性地合成了青霉烯醇 A1。青霉烯醇 A1 的 3-酰基四甲酸核心是通过 O-酰基到 C-酰基的重排成功构建的。
• Synthesis, stereochemical assignment, and bioactivity of the Penicillium metabolites penicillenols B1 and B2
  作者：Karl Kempf、Florian Schmitt、Ursula Bilitewski、Rainer Schobert

  DOI：10.1016/j.tet.2015.05.116

  日期：2015.8

  The Penicillium metabolites penicillenols B-1 and B-2 were synthesised for the first time by elimination of a mesylated penicillenol A precursor as obtained from an L-threonine derived tetramic acid. The (Z,S)-and (E,S)-configured diastereomers were identical to the natural compounds as to NMR spectra and optical rotations. Both isomers showed antiproliferative effects against cancer and endothelial cell lines and penicillenol B-1 was also notably antibiotic against Staphylococcus aureus. (C) 2015 Elsevier Ltd. All rights reserved.