(4S,8R)-11,13-dihydroxy-8-methoxy-4-methyl-1,4,5,6,7,8,9,10-octahydro-2H-3-benzoxacyclododecine-2,10-dione | 134933-23-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (4S,8R)-11,13-dihydroxy-8-methoxy-4-methyl-1,4,5,6,7,8,9,10-octahydro-2H-3-benzoxacyclododecine-2,10-dione
• 英文别名: (4S,8R)-11,13-dihydroxy-8-methoxy-4-methyl-4,5,6,7,8,9-hexahydro-1H-benzo[d][1]oxacyclododecine-2,10-dione；(4S,8R)-4,5,6,7,8,9-hexahydro-11,13-dihydroxy-8-methoxy-4-methyl-2H-3-benzoxacyclododecin-2,10(1H)-dione；β-11-methoxy curvularine；(11R,15S)-11-methoxycurvularin；11-β-methoxycurvularin；11β-methoxycurvularin；11Beta-Methoxycurvularin；(5S,9R)-13,15-dihydroxy-9-methoxy-5-methyl-4-oxabicyclo[10.4.0]hexadeca-1(12),13,15-triene-3,11-dione
• CAS: 134933-23-6
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: LBVPDFGFLMFDPI-GXFFZTMASA-N

物化性质

• 沸点：
  570.0±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  1
• 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：

  (2S,6S)-8-(benzyloxy)-6-methoxyoct-4-yn-2-yl (3,5-dimethoxyphenyl)acetate 在 Jones reagent 、 六氟乙酰丙酮 、 palladium 10% on activated carbon 、 氢气 、 碘 、 四丁基碘化铵 、 氢化铝 、 三氟乙酸 作用下， 以 乙酸乙酯 、 丙酮 、 苯 为溶剂， 反应 12.75h， 生成 (4S,8R)-11,13-dihydroxy-8-methoxy-4-methyl-1,4,5,6,7,8,9,10-octahydro-2H-3-benzoxacyclododecine-2,10-dione
  参考文献：
  名称：

  11β-甲氧基弯曲霉素的高效立体选择性全合成

  摘要：

  通过采用 Sharpless 不对称环氧化、由环氧氯化物形成炔丙醇和分子内 Friedel-Crafts 酰化作为关键步骤，实现了大环酮 11 β-甲氧基-curvularin 的非常短且有效的立体选择性全合成.

  DOI：

  10.3998/ark.5550190.p008.453

文献信息

• Stereoselective Total Synthesis of (11<i>β</i>)-11-Methoxycurvularin
  作者：Karuturi Rajesh、Vangaru Suresh、Jondoss Jon Paul Selvam、Dokuburra Chanti Babu、Yenamandra Venkateswarlu

  DOI：10.1002/hlca.200900136

  日期：2010.1

  A simple and highly efficient stereoselective total synthesis of (11β)‐11‐methoxycurvularin (5), a polyketide natural product, was achieved. The synthesis commenced with a Cu‐mediated regioselective opening of (2S)‐2‐methyloxirane (6) and comprised a Keck asymmetric allylation and intramolecular Friedel–Crafts acylation as key steps (Scheme 2).

  实现了一种简单，高效的立体选择性全合成（11β）-11-甲氧基弯曲素（5），这是一种聚酮化合物天然产物。合成开始于（2 S）-2-甲基环氧乙烷（6）的铜介导的区域选择性开放，并包括Keck不对称烯丙基化和分子内Friedel-Crafts酰化作为关键步骤（方案2）。
• New Curvularin-Type Metabolites from the Hybrid Strain ME 0005 Derived from<i>Penicillium Citreo-viride</i>B. IFO 4692 and 6200
  作者：Sheng Lai、Yoshikazu Shizuri、Shosuke Yamamura、Kazuaki Kawai、Hideyuki Furukawa

  DOI：10.1246/bcsj.64.1048

  日期：1991.3

  Four new curvularin-type metabolites (11-α-methoxycurvularin, 11-β-methoxy curvularin, 11,12-dihydroxycurvularin, and 12-hydroxy-10, 11-trans-dehydrocurvularin) have been isolated from the mycelium of the hybrid strain ME 0005 derived from Penicillium citreo-viride B. IFO 4692 and 6200. And β-hydroxycurvularin, the biologically active principle from Alternaria tomato, was identified as 11-β-hydroxycurvularin

  已从杂交菌株 ME 的菌丝体中分离出四种新的curvularin 型代谢物（11-α-甲氧基curvularin、11-β-甲氧基curvularin、11,12-dihydroxycurvularin 和12-hydroxy-10, 11-trans-dehydrocurvularin） 0005 来源于青霉属青霉 B. IFO 4692 和 6200。 β-羟基曲线素，来自 Alternaria 番茄的生物活性成分，被鉴定为 11-β-羟基曲线素。
• Stereoseletive Total Synthesis of 11-α- and 11-β-Methoxycurvularins
  作者：J. Yadav、A. Raju、K. Ravindar、B. Reddy

  DOI：10.1055/s-0029-1218621

  日期：2010.3

  Total synthesis of 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin has been accomplished in a highly stereoselective manner by utilizing Jacobsen hydrolytic kinetic resolution, Maruoka asymmetric allylation and intramolecular Friedel-Crafts acylation as key steps.
• First Total Syntheses and Spectral Data Corrections of 11-α-Methoxycurvularin and 11-β-Methoxycurvularin
  作者：Qiren Liang、Yongquan Sun、Binxun Yu、Xuegong She、Xinfu Pan

  DOI：10.1021/jo701885n

  日期：2007.12.1

  [Graphics]Concise and efficient total syntheses of 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin were accomplished for the first time. The three-component linchpin coupling and intramolecular acylation reactions were key steps, in which we found the spectral data of 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin, reported in the literature, were reversed with each other.
• Stereoselective syntheses of 11-α-methoxycurvularin and 11-β-methoxycurvularin
  作者：G. Venkateswar Reddy、R. Sateesh Chandra Kumar、K. Suresh Babu、J. Madhusudana Rao

  DOI：10.1016/j.tetlet.2009.04.120

  日期：2009.7

  A stereoselective synthesis of potent cytotoxic macrolides, 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin has been accomplished. The synthesis entailed Maruoka asymmetric allylation to introduce the stereocentres at C-11 and the key fragment was installed by using Grubbs cross-metathesis followed by CBS-reduction. (C) 2009 Published by Elsevier Ltd.