3-hydroxy-5-phenylmethyl-(3S,5R)-tetrahydrofuran-2-one

• 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: 3-hydroxy-5-phenylmethyl-(3S,5R)-tetrahydrofuran-2-one
• 英文别名: (3S,5R)-epi-harzialactone A；(2S,4R)-harzialactone A；(3S,5R)-5-benzyl-3-hydroxyoxolan-2-one
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: QDWGWZDQSRYLTG-ZJUUUORDSA-N

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

• 作为产物：
  描述：

  (+)-harzialactone A 在 甲醇 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 3-hydroxy-5-phenylmethyl-(3S,5R)-tetrahydrofuran-2-one
  参考文献：
  名称：

  Synthesis of harzialactone A and its isomers from d-glucose and assignment of absolute stereochemistry

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)00389-x

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）。
• A short synthesis of (+)-harzialactone A and (R)-(+)-4-hexanolide via proline-catalyzed sequential α-aminooxylation and Horner–Wadsworth–Emmons olefination of aldehydes
  作者：Shriram P. Kotkar、Gurunath S. Suryavanshi、Arumugam Sudalai

  DOI：10.1016/j.tetasy.2007.07.031

  日期：2007.8

  An efficient and short enantioselective synthesis of the antitumor marine metabolite, (+)-harzialactone A 1 and pheromone, (R)-(+)-4-hexanolide 2 using l-proline-catalyzed sequential α-aminooxylation and Horner–Wadsworth–Emmons olefination of the respective aldehydes is described.

  使用l-脯氨酸催化的连续α-氨氧基化和Horner-Wadsworth-Emmons高效和短时对映选择性合成抗肿瘤海洋代谢物（+）-哈兹内酯A 1和信息素（R）-（+）-4-己内酯2描述了各个醛的烯烃化。
• 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。
• Cascade Synthesis of Five-Membered Lactones using Biomass-Derived Sugars as Carbon Nucleophiles
  作者：Sho Yamaguchi、Takeaki Matsuo、Ken Motokura、Akimitsu Miyaji、Toshihide Baba

  DOI：10.1002/asia.201600307

  日期：2016.6.6

  We report the cascade synthesis of five‐membered lactones from a biomass‐derived triose sugar, 1,3‐dihydroxyacetone, and various aldehydes. This achievement provides a new synthetic strategy to generate a wide range of valuable compounds from a single biomass‐derived sugar. Among several examined Lewis acid catalysts, homogeneous tin chloride catalysts exhibited the best performance to form carbon–carbon

  我们报道了从生物质衍生的三糖，1,3-二羟基丙酮和各种醛类中五元内酯的级联合成。这项成就提供了一种新的合成策略，可以从一种生物质衍生的糖中产生多种有价值的化合物。在几种经过检验的路易斯酸催化剂中，均相氯化锡催化剂表现出形成碳-碳键的最佳性能。研究了使用醛类化合物合成五元内酯的范围和局限性。级联反应导致高产物选择性和非对映选择性，并基于异构化实验和密度泛函理论（DFT）计算，讨论了导致非对映选择性的机理。
• Oxone®-Mediated Direct α-Hydroxylation of β-Dicarbonyl Compounds: Racemic Synthesis of Harzialactone A
  作者：Marcus Sá、Marcos Peterle、Marcelo Marques

  DOI：10.21577/0103-5053.20190082

  日期：——

  An environmentally benign method is described for the alpha-hydroxylation of malonates and cyclic analogues in aqueous medium at room temperature under mild conditions, based on the in situ generation of dimethyldioxirane through the combination of acetone and Oxon (R). This procedure was found to be substrate-dependent and was successfully performed to provide alpha-hydroxylated gamma-lactones. To demonstrate the synthetic potential of this mild alpha-hydroxylation, two different concise mutes were developed to synthesize harzialactone A in the racemic form with a moderate (3:1) diastereomeric ratio.