harzialactone A | 321868-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: harzialactone A
• 英文别名: trans-(+)-harzialactone A；3-hydroxy-5-phenylmethyl-(3S,5S)-tetrahydrofuran-2-one；(3S,5S)-5-benzyl-3-hydroxyoxolan-2-one
• CAS: 321868-49-9
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: QDWGWZDQSRYLTG-UWVGGRQHSA-N

物化性质

• 熔点：
  73-75 °C
• 沸点：
  360.1±17.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-α-甲氧基-α-(三氟甲基)苯乙酸 、 harzialactone A 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 harzialactone A (S)-MPPA ester
  参考文献：
  名称：

  海绵的真菌菌株产生的细胞毒性物质：理化性质和结构。

  摘要：

  从最初分离的哈茨木霉OUPS-N115菌株的培养液中分离出了五种新陈代谢产物，即曲古烯AC（1-3），哈兹内酯A（4）和B（5）以及已知的R-甲羟内酯（6）。从海绵Halichondria okadai。光谱证据已经阐明了它们的结构。其中，1-3显示出对培养的P388细胞的显着细胞毒性。

  DOI：

  10.7164/antibiotics.51.33
• 作为产物：
  描述：

  (S)-2,4-Dihydroxy-5-phenyl-pentanoic acid methyl ester 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 以31 mg的产率得到harzialactone A
  参考文献：
  名称：

  An expeditious route to the antipode of harzialactone A

  摘要：

  The antipode of the antitumor marine metabolite harzialactone A was synthesized from L-malic acid via a very efficient route in 40% overall yield involving only two chromatographic separations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.003

文献信息

• New synthesis of harzialactone A via kinetic resolution using recombinant Fusarium proliferatum lactonase
  作者：Bing Chen、Hai-Feng Yin、Zhen-Sheng Wang、Jian-He Xu

  DOI：10.1016/j.tetasy.2010.01.021

  日期：2010.2

  A new synthesis of harzialactone A together with its stereoisomers was achieved starting from phenyl acetone. The key step of this new route is the kinetic bioresolution of racemic cis- and trans-isomers by recombinant Escherichia coli JM109 cells expressing Fusarium proliferatum lactonase gene (reFPL). Harzialactone A was isolated in excellent ee (>99%), while moderate to good enantioselectivities

  从苯丙酮开始，实现了对苯乙内酯A及其立体异构体的新合成。此新途径的关键步骤是表达镰刀菌增生性内酯酶基因（reFPL）的重组大肠杆菌JM109细胞对外消旋顺式和反式异构体的动力学生物拆分。在优异的ee（> 99％）中分离出Harzialactone A，同时获得了其异构体的中等至良好的对映选择性（80％至> 99％ee）。
• Stereocontrolled Synthesis of Harzialactone A and Its Three Stereoisomers by Use of Standardized Polyketide Building Blocks
  作者：Frederic Ballaschk、Yasemin Özkaya、Stefan F. Kirsch

  DOI：10.1002/ejoc.202001046

  日期：2020.10.15

  The Harzialactone A synthesis utilizes a Horner–Wittig‐reaction of the chiral building block and benzaldehyde in the first step. The formed β‐hydroxy ketone can be selectively transformed into the syn‐ or anti‐diol, which is further converted into the desired natural compound by ozonolysis, cyclization and oxidation in one step.

  第一步，Harzialactone A合成利用手性结构单元和苯甲醛的Horner-Wittig反应。形成的β-羟基酮可以选择性地转化为顺式或反式二醇，然后通过臭氧分解，环化和氧化一步转化为所需的天然化合物。
• Chemoenzymatic asymmetric synthesis of harzia lactone A stereomers
  作者：Abha N. Kumar、Suchitra Bhatt、Subrata Chattopadhyay

  DOI：10.1016/j.tetasy.2009.01.009

  日期：2009.2

  A facile chemoenzymatic synthesis of the harzia lactone A enantiomers was developed. A lipase-catalyzed acylation and an enantio-controlled substrate and reagent-con trol led Sharpless' asymmetric dihydroxylation are the key features of the synthesis. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of harzialactone A and its isomers from d-glucose and assignment of absolute stereochemistry
  作者：Hari Babu Mereyala、Maju Joe、Rajendrakumar Reddy Gadikota

  DOI：10.1016/s0957-4166(00)00389-x

  日期：2000.10

  The synthesis of the marine metabolite (3R,5R)-harzialactone A 1 from D-glucose is described. Syntheses of all the isomers (3S,5R)-2, (3R,5S)-3 and (3S,5S)-4 of 1 are also described and the absolute stereochemistry for the natural product 1 is assigned unambiguously. (C) 2000 Elsevier Science Ltd. All rights reserved.
• NEW PRODUCT
  申请人：ALPHA BIOPESTICIDES LIMITED

  公开号：US20180146683A1

  公开（公告）日：2018-05-31

  The invention provides an agrochemical composition comprising: (a) one or more fatty acids or derivatives thereof; and (b) a strain, culture, culture filtrate, spores or mycelia of a species of a fungus or oomycete, or a metabolite produced by a species of a fungus or oomycete, which strain, culture, culture filtrate, spores, mycelia or metabolite directly or indirectly (i) inhibits the growth or reproduction of plant pathogens or (ii) kills plant pathogens. Also provided is a method for controlling fungi or oomycetes at a locus, a method for promoting growth in a plant and a method for controlling nematodes at a locus.