(+)-cephalosporolide B | 97344-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奥昔康唑
• 英文名称: (+)-cephalosporolide B
• 英文别名: cephalosporolide B；Cephalosporolide B；(2R,6Z,8S)-8-hydroxy-2-methyl-3,4,8,9-tetrahydro-2H-oxecine-5,10-dione
• CAS: 97344-03-1
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: OYHHNJLVXIIQGO-LEZDYHIDSA-N

物化性质

• 沸点：
  427.2±45.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-cephalosporolide B 在 双氧水 、 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 以84%的产率得到(+)-cephalosporolide B
  参考文献：
  名称：

  Cephalosporolide B Serving as a Versatile Synthetic Precursor: Asymmetric Biomimetic Total Syntheses of Cephalosporolides C, E, F, G, and (4-OMe-)G

  摘要：

  Cephalosporolide B (Ces-B) was efficiently synthesized and exploited for the first time as a versatile biomimetic synthetic precursor for the chemical syntheses of not only cephalosporolides C, G, and (4-OMe-) G via a challenging diastereoselective oxa-Michael addition but also the structurally unprecedented cephalosporolides E and F via a novel biomimetic ring-contraction rearrangement. These findings provide the first direct chemical evidence that Ces-B may be the true biosynthetic precursor of cephalosporolides.

  DOI：

  10.1021/ol402913m
• 作为产物：
  描述：

  (2R,4aS,7S,8aS)-7-(tert-butyldimethylsilyloxy)-4a-hydroxy-2-methyl-3,4,4a,7,8,8a-hexahydrobenzo-1(2H)-pyran 在 2-叠氮丙二酸二甲酯 、 Rh₂(OAc)4 、 sodium acetate 、 氟化氢吡啶 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 2.0h， 生成 (+)-cephalosporolide B
  参考文献：
  名称：

  Cephalosporolide B Serving as a Versatile Synthetic Precursor: Asymmetric Biomimetic Total Syntheses of Cephalosporolides C, E, F, G, and (4-OMe-)G

  摘要：

  Cephalosporolide B (Ces-B) was efficiently synthesized and exploited for the first time as a versatile biomimetic synthetic precursor for the chemical syntheses of not only cephalosporolides C, G, and (4-OMe-) G via a challenging diastereoselective oxa-Michael addition but also the structurally unprecedented cephalosporolides E and F via a novel biomimetic ring-contraction rearrangement. These findings provide the first direct chemical evidence that Ces-B may be the true biosynthetic precursor of cephalosporolides.

  DOI：

  10.1021/ol402913m

文献信息

• Concise Enantioselective Synthesis of Cephalosporolide B, (4<i>R</i>)-4-OMe-Cephalosporolide C, and (4<i>S</i>)-4-OMe-Cephalosporolide C
  作者：Bin Ma、Zhuliang Zhong、Haitao Hu、Huilin Li、Changgui Zhao、Xingang Xie、Xuegong She

  DOI：10.1002/asia.201300332

  日期：2013.7

  Ring around the rosie: The effective enantioselective synthesis of the antimalarial nonenolide title compounds was achieved in a convergent strategy. Oxy‐Michael addition reaction was used to introduce the chiral methoxy group at C‐4, and ring‐closing metathesis (RCM) reaction (53 % yield) facilitated the key construction of the 10‐membered ring.

  围绕玫瑰红：以收敛策略有效地合成了抗疟的壬烯内酯标题化合物。使用Oxy-Michael加成反应在C-4处引入手性甲氧基，开环复分解（RCM）反应（产率53％）促进了10元环的关键构建。
• Ackland, Mark J.; Hanson, James R.; Hitchcock, Peter B., Journal of the Chemical Society. Perkin transactions I, 1985, p. 843 - 848
  作者：Ackland, Mark J.、Hanson, James R.、Hitchcock, Peter B.、Ratcliffe, Arnold H.

  DOI：——

  日期：——
• Cephalosporolide B Serving as a Versatile Synthetic Precursor: Asymmetric Biomimetic Total Syntheses of Cephalosporolides C, E, F, G, and (4-OMe-)G
  作者：Liyan Song、Yuan Liu、Rongbiao Tong

  DOI：10.1021/ol402913m

  日期：2013.11.15

  Cephalosporolide B (Ces-B) was efficiently synthesized and exploited for the first time as a versatile biomimetic synthetic precursor for the chemical syntheses of not only cephalosporolides C, G, and (4-OMe-) G via a challenging diastereoselective oxa-Michael addition but also the structurally unprecedented cephalosporolides E and F via a novel biomimetic ring-contraction rearrangement. These findings provide the first direct chemical evidence that Ces-B may be the true biosynthetic precursor of cephalosporolides.