(-)-pregaliellalactone | 408311-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (-)-pregaliellalactone
• 英文别名: (2R)-2-but-3-enyl-4-[(E)-prop-1-enyl]-2H-furan-5-one
• CAS: 408311-40-0
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: BJPQUMCGDYCEDF-DFVUYQKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-pregaliellalactone 在 Galiella rufa mycelium 、 sodium chloride 作用下， 以 甲醇 、 水 为溶剂， 以90%的产率得到galiellalactone
  参考文献：
  名称：

  Synthesis of (−)-pregaliellalactone, conversion of (−)-pregaliellalactone to (−)-galiellalactone by mycelia of Galiella rufa

  摘要：

  An enantioselective synthesis of (-)-pregaliellalactone (1), a biosynthetic precursor of the potent fungal metabolite ( -)-galiellalactone (3) produced by several ascomycetes, is reported. When fed to a culture of Galiella rufa, 1 was efficiently converted to 3. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00134-5
• 作为产物：
  描述：

  ethyl 7-(tert-butyldimethylsilyloxy)-4-hydroxyhept-2-ynoate 在 四(三苯基膦)钯 (IMes)CuCl 、 碘 、 三正丁基氢锡 、 乙酰氯 、 三苯基膦 、 异丙醇 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 四氯化碳 、 二甲基亚砜 为溶剂， 反应 34.0h， 生成 (-)-pregaliellalactone
  参考文献：
  名称：

  Copper-Catalyzed Methylenation Reaction:  Total Synthesis of (+)-Desoxygaliellalactone

  摘要：

  The enantioselective total synthesis of (+)-desoxygaliellalactone was achieved in six steps starting from 4-tert-butyldimethylsilyloxybutanal. This synthesis featured a one-pot copper-catalyzed methylenation-Diels-Alder cyclization. The challenging methylenation of aldehyde 4 was studied under various reaction conditions. Whereas Wittig reaction conditions led to byproducts resulting from decomposition of the sensitive butenolide moiety, the mild copper-catalyzed methylenation reaction produced the desired triene in good yield.

  DOI：

  10.1021/ol071391q

文献信息

• An efficient synthesis of pregaliellalactone and desoxygaliellalactone
  作者：Eira Ruud Furuseth、Rikard Larsson、Narda Blanco、Martin Johansson、Olov Sterner

  DOI：10.1016/j.tetlet.2014.04.117

  日期：2014.7
• Cyclization of (−)-Pregaliellalactone in the Fungus Galiella rufa
  作者：Martin Johansson、Bärbel Köpcke、Heidrun Anke、Olov Sterner

  DOI：10.1002/1521-3773(20020617)41:12<2158::aid-anie2158>3.0.co;2-p

  日期：2002.6.17
• Synthesis of (−)-pregaliellalactone, conversion of (−)-pregaliellalactone to (−)-galiellalactone by mycelia of Galiella rufa
  作者：Martin Johansson、Bärbel Köpcke、Heidrun Anke、Olov Sterner

  DOI：10.1016/s0040-4020(02)00134-5

  日期：2002.3

  An enantioselective synthesis of (-)-pregaliellalactone (1), a biosynthetic precursor of the potent fungal metabolite ( -)-galiellalactone (3) produced by several ascomycetes, is reported. When fed to a culture of Galiella rufa, 1 was efficiently converted to 3. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Copper-Catalyzed Methylenation Reaction:  Total Synthesis of (+)-Desoxygaliellalactone
  作者：Hélène Lebel、Michaël Parmentier

  DOI：10.1021/ol071391q

  日期：2007.8.1

  The enantioselective total synthesis of (+)-desoxygaliellalactone was achieved in six steps starting from 4-tert-butyldimethylsilyloxybutanal. This synthesis featured a one-pot copper-catalyzed methylenation-Diels-Alder cyclization. The challenging methylenation of aldehyde 4 was studied under various reaction conditions. Whereas Wittig reaction conditions led to byproducts resulting from decomposition of the sensitive butenolide moiety, the mild copper-catalyzed methylenation reaction produced the desired triene in good yield.