(-)-kusunokinin

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (-)-kusunokinin
• 英文别名: (2R,3R)-3-(3,4-dimethoxybenzyl)-2-(3,4-methylenedioxybenzyl)-butyrolactone；Kusunokinin；(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: LEVKKQBBEVGIKN-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-kusunokinin 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 (8R,8'R)-3',4'-dimethoxy-3,4-methylenedioxylignano-9,9'-thionolactone
  参考文献：
  名称：

  Discovery of stereospecific cytotoxicity of (8R,8′R)-trans-arctigenin against insect cells and structure-activity relationship on aromatic ring

  摘要：

  One of the arctigenin stereoisomers, (8R,8'R)-trans-form 1, showed stereospecific cytotoxicity against insect cells, Sf9 and NIAS-AeAl-2 cells. By the comparison with other stereoisomers, the most importance of the 8'R stereochemistry for the higher activities was clarified. On the other hand, the wider range of activity level among stereoisomers against cancer cells, HL-60, was not observed. The structure-activity relationship research using derivatives bearing (8R,8'R)-trans-form was performed to show the same level of activities of 3-iodo, 4-iodo, and 3,4-methylenedioxy derivatives 28, 29, and 36 as (8R,8'R)-trans-arctigenin 1. In the examination of thiono derivatives, 4-iodo thiono and 3,4-methylenedioxy thiono derivatives 66, 67 showed similar level of activities to that of (8R,8'R)-trans-arctigenin 1. The expression of ribosomal 28S rRNA gene of Sf9 cells was increased by (8R,8'R)-trans-arctigenin 1, whereas a degradation of DNA was not observed.

  DOI：

  10.1016/j.bmcl.2020.127191
• 作为产物：
  描述：

  ((3,4-dimethoxyphenyl)methylene)bis(phenylsulfane) 在 氢氧化钾 、 sodium tetrahydroborate 、 正丁基锂 、 地昔帕明 、 nickel dichloride 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 12.5h， 生成 (-)-kusunokinin
  参考文献：
  名称：

  Pelter, Andrew; Ward, Robert S.; Jones, Martin D., Journal of the Chemical Society. Perkin transactions I, 1993, # 21, p. 2631 - 2638

  摘要：

  DOI：

文献信息

• Lignames
  作者：Eric Brown、Alain Daugan

  DOI：10.1016/0040-4020(89)80041-9

  日期：1989.1

  following two lactones were obtained in both (R)-(+) and (S)-(−) enantiomeric forms, β-piperonyl- and β-veratryl-γ-butyrolactones and respectively. These lactones were used as key-intermediates for the syntheses of 17 optically active lignans and lignoids, such as (-1-dimethylmatairesinol (−)-, (−)-kusunokinin (−)- and (+)-diniethylisolariciresinol (+)-.

  描述了导致光学活性的β-苄基-γ-丁内酯的简单而有效的途径。因此，由Stobbe与适当的芳族醛缩合，然后催化氢化中间体α-亚苄基半琥珀酸酯而得到的（R，S）-α-苄基双琥珀酸甲酯，通过手性碱（麻黄碱或α-乙胺基）。使用硼氢化钙还原每种对映异构体，然后得到相应的旋光性β-苄基-γ-丁内酯。以此方式，以（R）-（+）和（S）-（-）对映体形式获得以下两个内酯，β-哌啶基-和β-藜芦基-γ-丁内酯和分别。这些内酯用作合成17种旋光性木脂素和木质素的关键中间体，例如（-1-二甲基麦芽甾醇（-）- ，（-）-苦参素（-）-和（+）-二乙基异芳基树脂（+）- 。
• Asymmetric Chemoenzymatic Synthesis of (−)‐Podophyllotoxin and Related Aryltetralin Lignans
  作者：Jian Li、Xiao Zhang、Hans Renata

  DOI：10.1002/anie.201904102

  日期：2019.8.19

  (−)‐Podophyllotoxin is one of the most potent microtubule depolymerizing agents and has served as an important lead compound in antineoplastic drug discovery. Reported here is a short chemoenzymatic total synthesis of (−)‐podophyllotoxin and related aryltetralin lignans. Vital to this approach is the use of an enzymatic oxidative C−C coupling reaction to construct the tetracyclic core of the natural

  （-）-鬼臼毒素是最有效的微管解聚剂之一，在抗肿瘤药物的发现中起着重要的先导化合物的作用。这里报道的是（-）-鬼臼毒素和相关芳基四氢木脂素的短促化学酶法全合成。这种方法的关键是使用酶促氧化性C-C偶联反应以非对映选择性的方式构建天然产物的四环核。该策略允许以克级获得（-）-脱氧鬼臼毒素，并且很容易适应相关芳基四氢木脂素的制备。
• (R)-(+)-β-Veratryl-γ-butyrolactone. A new key-intermediate for the asymmetric synthesis of various lignans
  作者：Eric Brown、Alain Daugan

  DOI：10.1016/s0040-4039(00)83862-9

  日期：1986.1

  α-veratrylhemisuccinate was resolved into its (R)-(+) and (S)-(−) antipodes by (S)-(−) and (R)-(+)-α-methylbenzylamine respectively. Calcium borohydride reduction of the (R)-(+)-hemiester afforded (R)-(+)-β-veratryl-γ-butyrolactone. The latter was used for the synthesis of various naturlly occurring lignans such as (+)-dimethylisolariciresinol, (−)-kusunokinin and (−)-dimethylmatairesinol.

  α-藜芦基琥珀酸甲酯分别通过（S）-（-）和（R）-（+）-α-甲基苄基胺分解为（R）-（+）和（S）-（-）对映体。（R）-（+）-半胱氨酸的硼氢化钙还原得到（R）-（+）-β-藜芦基-γ-丁内酯。后者被用于合成各种天然存在的木脂素，例如（+）-二甲基异拉西里醇，（-）-苦参素和（-）-二甲基马来甾醇。
• Asymmetric syntheses of lignans of the dibenzylbutyrolactone, dibenzylbutanediol, aryltetraun and dibenzocyclooctadiene series
  作者：Andrew Pelter、Robert S. Ward、D.Martin Jones、Peter Maddocks

  DOI：10.1016/s0957-4166(00)80200-1

  日期：1992.1

  General procedures are outlined for the asymmetric syntheses of lignans of the dibenzylbutyrolactone, dibenzylbutanediol, aryltetralin and dibenzocyclooctadiene series, from tandem addition products derived from 4-menthyloxybutenolide.
• MORITANI, YASUNORI;UKITA, TATSUZO;NISHITANI, TAKASHI;SEKI, MASAHIKO;IWASA+, TETRAHEDRON LETT., 31,(1990) N5, C. 3615-3618
  作者：MORITANI, YASUNORI、UKITA, TATSUZO、NISHITANI, TAKASHI、SEKI, MASAHIKO、IWASA+

  DOI：——

  日期：——