(+/-)-pandamarilactonine-A

• 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: (+/-)-pandamarilactonine-A
• 英文别名: pandamarilactonine-A；(5Z)-3-Methyl-5-[4-[(2S)-2-[(2S)-4-methyl-5-oxo-2H-furan-2-yl]pyrrolidin-1-yl]butylidene]furan-2-one
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: HSICZNIIIPFAAO-FQJVJMQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-甲基-2(5H)-呋喃酮 在 碘代三甲硅烷 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 130.0h， 生成 (+/-)-pandamarilactonine-A
  参考文献：
  名称：

  露兜树生物碱的合成研究：从去甲大马里内酯到大马内酯，证明它们的构型不稳定性

  摘要：

  从 (S)-脯氨醇开始，以对映体纯的形式制备去甲潘丹马里内酯-A 的氨基甲酸乙酯。胺官能团的脱保护使非对映异构体去甲熊猫内酯均成为外消旋物，用作熊猫内酯-A和-B的合成前体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200300474

文献信息

• Novel stereoselective synthesis of enantiopure (+)-N-Boc-norpandamarilactonine-A, the intermediate for pandamarilactonines
  作者：Toshio Honda、Makoto Ushiwata、Hirotake Mizutani

  DOI：10.1016/j.tetlet.2006.06.142

  日期：2006.8

  A novel synthesis of enantiopure N-Boc-norpandamarilactonine-A was established by employing a double ring-closing metathesis of a tetraene derivative, as a key step, where two five-membered rings were constructed in one step. N-Boc-Norpandamarilactonine-A was also converted to ent-norpandamarilactonine-A, and subsequently to pandamarilactonine-A and B.

  通过采用四烯衍生物的双闭环复分解反应作为关键步骤，建立了对映纯N -Boc-norpandamarilactonine- A的新型合成方法，其中一步构建了两个五元环。N -Boc-Norpandamarilactonine-A也被转化为ent -norpandamarilactonine-A，随后又被转化为pandamarilactonine-A和B。
• Total synthesis of four Pandanus alkaloids: pandamarilactonine-A and -B and their chemical precursors norpandamarilactonine-A and -B
  作者：Félix Busqué、Pedro de March、Marta Figueredo、Josep Font、Elena Sanfeliu

  DOI：10.1016/s0040-4039(02)01129-2

  日期：2002.8

  Norpandamarilactonine-A and -B are prepared from (S)-prolinol and converted into pandamarilactonine-A and -B.

  由（S）-脯氨醇制备去甲扁桃酸内酯-A和-B，并将其转化为pandamarilactonine-A和-B。
• Isolation and Structure Elucidation of Two New Alkaloids, Pandamarilactonine-C and -D, from Pandanus amaryllifolius and Revision of Relative Stereochemistry of Pandamarilactonine-A and -B by Total Synthesis.
  作者：Hiromitsu Takayama、Tomotake Ichikawa、Mariko Kitajima、Maribel G. Nonato、Norio Aimi

  DOI：10.1248/cpb.50.1303

  日期：——

  Two new pyrrolidine alkaloids, pandamarilactonine-C and -D, were isolated from Pandanus amaryllifolius. Based on the total synthesis of pandamarilactonine-C and its related alkaloid, pandamarilactonine-A, the relative stereochemistry of pandamarilactonine-A and -B, which was previously proposed by spectroscopic analysis, was revised.

  从露兜树中分离出两种新的吡咯烷生物碱，pandamarilactonine-C和-D。在对pandamarilactonine-C及其相关生物碱pandamarilactonine-A进行全合成的基础上，修订了以前通过光谱分析提出的pandamarilactonine-A和-B的相对立体化学。
• Synthetic Studies onPandanus Alkaloids: From Norpandamarilactonines to Pandamarilactonines, a Proof of Their Configurational Instability
  作者：Pilar Blanco、Felix Busqué、Pedro de March、Marta Figueredo、Josep Font、Elena Sanfeliu

  DOI：10.1002/ejoc.200300474

  日期：2004.1

  The ethyl carbamate of norpandamarilactonine-A was prepared in an enantiomerically pure form starting from (S)-prolinol. Deprotection of the amine functionality rendered both diastereomeric norpandamarilactonines as racemates, which were used as synthetic precursors of pandamarilactonine-A and -B. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  从 (S)-脯氨醇开始，以对映体纯的形式制备去甲潘丹马里内酯-A 的氨基甲酸乙酯。胺官能团的脱保护使非对映异构体去甲熊猫内酯均成为外消旋物，用作熊猫内酯-A和-B的合成前体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)