curvulone B | 1263694-22-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: curvulone B
• 英文别名: methyl 2-[3,5-dihydroxy-2-[2-[(2R,6R)-6-methyloxan-2-yl]acetyl]phenyl]acetate
• CAS: 1263694-22-9
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: HLONHEIIGSDLQH-ZWNOBZJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,5-二苄氧基苯甲醇 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 bis-triphenylphosphine-palladium(II) chloride 、 氯化亚砜 、 20% palladium hydroxide-activated charcoal 、 氢气 、 四氯化锡 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 六氟苯 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 11.0h， 生成 curvulone B
  参考文献：
  名称：

  Synthesis of Curvulone B Using the 2-Chlorobenzyl Protecting Group

  摘要：

  A total synthesis of curvulone B has been completed using a Friedel-Crafts reaction and a highly cis-selective intramolecular oxa-Michael addition. The 2-chlorobenzyl protecting group was employed and found to have much greater Lewis acid stability compared to the simple benzyl group.

  DOI：

  10.1055/s-0034-1379988

文献信息

• Concise Total Synthesis of Curvulone B
  作者：Debendra K. Mohapatra、Shivalal Banoth、Utkal Mani Choudhury、Kanakaraju Marumudi、Ajit C. Kunwar

  DOI：10.1055/a-1297-6838

  日期：2021.4

  A concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts

  描述了curvulone B 的简洁和收敛立体选择性合成。该合成利用串联异构化，然后在 Mukaiyama 型羟醛条件下进行 C-O 和 C-C 键形成反应，以构建反式-2,6-二取代二氢吡喃环系统作为关键步骤。这种合成的其他重要特征是交叉复分解、差向异构化和 Friedel-Crafts 酰化。
• Total synthesis of curvulone B and a proposed structure for dothiorelone B; determination of the configuration of curvulone B and structural revision of phomopsin A
  作者：Shunya Takahashi、Yuki Akita、Takemichi Nakamura、Hiroyuki Koshino

  DOI：10.1016/j.tetasy.2012.06.009

  日期：2012.7

  The total synthesis of curvulone B was achieved, and its absolute configuration unambiguously established, as had been determined by TD-DFT ECD calculations on the computed solution conformers. Key features of the synthesis were an olefin cross-metathesis of an α,β-unsaturated ketone as a common key building block with (R)-6-triethylsilyloxyhept-1-ene, and an intramolecular oxy-Michael addition of

  如通过TD-DFT ECD计算得出的解决方案构象异构体所确定的那样，实现了曲妥酮B的全合成，并明确建立了其绝对构型。合成的关键特征是与（R）-6-三乙基甲硅烷基氧基庚1烯作为共同关键结构单元的α，β-不饱和酮的烯烃交叉复分解，以及获得的羟基烯酮的分子内氧-迈克尔加成反应由此。烯酮与（S）-5-苄氧基庚烯的分子间复分解反应也使我们能够制备拟议的多硫瑞龙B的结构，从而证实了新的九元环状苯酚醚磷脂A的结构变化。
• A Unified Synthetic Approach to Optically Pure Curvularin-Type Metabolites
  作者：Srinivasa Rao Allu、Sreenivas Banne、Jia Jiang、Na Qi、Jian Guo、Yun He

  DOI：10.1021/acs.joc.9b00776

  日期：2019.6.7

  A unified and concise approach to the synthesis of nine curvularin-type metabolites and two analogues has been developed with few steps and high yields. Among them, sumalactones A–D were synthesized for the first time. The key steps in this approach included esterification, Friedel–Crafts acylation, and ring-closing metathesis (or cross metathesis).

  已经开发出了一种统一，简洁的方法来合成九种卡维拉林型代谢物和两种类似物，且步骤少且产率高。其中，舒马内酯A–D是首次合成。该方法的关键步骤包括酯化，Friedel-Crafts酰化和闭环易位（或交叉易位）。