berkeleyamide A | 1019854-19-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: berkeleyamide A
• 英文别名: (10S,11R,14S)-berkeleyamide A；(3R,5S)-3-[(1S)-1-hydroxy-3-oxo-4-phenylbutyl]-5-(2-methylpropyl)pyrrolidin-2-one
• CAS: 1019854-19-3
• 化学式: C₁₈H₂₅NO₃
• 分子量: 303.401
• InChiKey: KACACYYTPVUKSL-UAGQMJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  berkeleyamide A 在 吡啶 、 乙酸酐 作用下， 反应 24.0h， 以2.1 mg的产率得到[(1S)-1-[(3R,5S)-5-(2-methylpropyl)-2-oxopyrrolidin-3-yl]-3-oxo-4-phenylbutyl] acetate
  参考文献：
  名称：

  The Berkeleyamides, Amides from the Acid Lake Fungus Penicillum rubrum

  摘要：

  We previously reported several novel bioactive hybrid polyketide-terpenoid metabolites from a deep water Penicillium rubrum isolated from Berkeley Pit Lake, Butte, Montana. In this paper we report the structures of four new amides, berkeleyamides A-D (1, 4, 5, 7), isolated from extracts of this fungus. The structures of these compounds were deduced by analysis of NMR data, chemical derivatization, and comparison of their spectroscopic data to those of known compounds.

  DOI：

  10.1021/np0705054
• 作为产物：
  描述：

  (3R,5S)-3-[(1S)-2-(2-benzyl-1,3-dioxolan-2-yl)-1-hydroxyethyl]-5-isobutylpyrrolidin-2-one 在 双(乙腈)氯化钯(II) 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 以77%的产率得到berkeleyamide A
  参考文献：
  名称：

  Asymmetric Total Synthesis of the Caspase-1 Inhibitor (−)-Berkeleyamide A

  摘要：

  The asymmetric total synthesis of (-)-berkeleyamide A (1), a naturally occurring caspase-1 inhibitor, has been achieved by employing Evans' syn- aldol reaction of N-acyl-(4R)-benzyl oxazolidin-2-one 3 as the key step.

  DOI：

  10.1021/jo1001033

文献信息

• Total Synthesis of Berkeleyamide A and its 10-epi Isomer
  作者：Narayan S. Chakor、Sabrina Dallavalle、Leonardo Scaglioni、Lucio Merlini

  DOI：10.1002/ejoc.201000914

  日期：2010.11

  A short and efficient synthesis of the novel cytotoxic natural product berkeleyamide A, isolated from a deep-water Penicillium rubrum, has been accomplished. L -Leucinol was used as the only chiral starting material. A diastereoselective aldol condensation is the key step in the synthesis.

  从深水红色青霉中分离出的新型细胞毒性天然产物伯克利酰胺 A 的简短有效合成已经完成。L-亮氨酸被用作唯一的手性原料。非对映选择性羟醛缩合是合成中的关键步骤。
• Total Synthesis and Absolute Configuration of (−)-Berkeleyamide A
  作者：Jonathan Sperry、Eric B. J. Harris、Margaret A. Brimble

  DOI：10.1021/ol902525k

  日期：2010.2.5

  A chiral-pool approach to (−)-berkeleyamide A 1 based on a diastereoselective nitrile oxide [3 + 2]-cycloaddition completes the first total synthesis establishing the absolute stereochemistry of the natural product.

  基于非对映选择性腈[3 + 2]-环加成的（-）-苯甲酰胺A 1的手性池方法完成了第一个总合成，建立了天然产物的绝对立体化学。
• Asymmetric Total Synthesis of the Caspase-1 Inhibitor (−)-Berkeleyamide A
  作者：Swapnil J. Kulkarni、Yakambram Pedduri、Amar G. Chittiboyina、Mitchell A. Avery

  DOI：10.1021/jo1001033

  日期：2010.5.7

  The asymmetric total synthesis of (-)-berkeleyamide A (1), a naturally occurring caspase-1 inhibitor, has been achieved by employing Evans' syn- aldol reaction of N-acyl-(4R)-benzyl oxazolidin-2-one 3 as the key step.
• The Berkeleyamides, Amides from the Acid Lake Fungus <i>Penicillum rubrum</i>
  作者：Andrea A. Stierle、Donald B. Stierle、Brianna Patacini

  DOI：10.1021/np0705054

  日期：2008.5.1

  We previously reported several novel bioactive hybrid polyketide-terpenoid metabolites from a deep water Penicillium rubrum isolated from Berkeley Pit Lake, Butte, Montana. In this paper we report the structures of four new amides, berkeleyamides A-D (1, 4, 5, 7), isolated from extracts of this fungus. The structures of these compounds were deduced by analysis of NMR data, chemical derivatization, and comparison of their spectroscopic data to those of known compounds.