(+)-podototarin | 2539-02-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-podototarin
• 英文别名: (4bS,8aS)-3-[(4bS,8aS)-2-hydroxy-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl]-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol
• CAS: 2539-02-8
• 化学式: C₄₀H₅₈O₂
• 分子量: 570.899
• InChiKey: RFUVOURUUJLQSB-QGJJZOTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4bS)-反式-8,8-三甲基-4b,5,6,7,8,8a,9,10-八氢-1-异丙基菲-2-醇 生成 (+)-podototarin
  参考文献：
  名称：

  罗汉松科化学-VIII：大叶酸，一种来自罗汉松D. Don的双二萜。

  摘要：

  从心材Macrophyllic酸罗汉松已被证明是bisditerpenoid二羧酸（我，- [R  ħ）有关podototarin，其二-O-甲基二甲基酯等合成从16羟基桃拓酚。Podototarin（IV，- [R  CH 3）已经被制备（+）的一步骤酶促偶联-桃拓酚以及在偶联反应扩展macrophyllic酸二甲酯的氢化铝锂还原产物的制备。

  DOI：

  10.1016/s0040-4020(01)99366-4

文献信息

• Iodination of Thallium(I) Salts of Phenols
  作者：Richard C. Cambie、David S. Larsen、Peter S. Rutledge、Paul D. Woodgate

  DOI：10.1071/c97051

  日期：——

  The iodination of thallium(I) salts of phenols is examined and the results are compared with those of the selective ortho-iodinating reagent thallium(I) acetate-iodine.

  对苯酚铊(I)盐的碘化作用进行了研究，并将结果与选择性邻位碘化试剂铊(I)乙酸盐-碘进行了比较。
• Chemistry of the podocarpaceae—VIII
  作者：S.M. Bocks、R.C. Cambie、T. Takahashi

  DOI：10.1016/s0040-4020(01)99366-4

  日期：1963.1

  Macrophyllic acid from the heartwood of Podocarpus macrophyllus has been shown to be the bisditerpenoid dicarboxylic acid (I, R  H) related to podototarin, and its di-O-methyl dimethyl ester synthesized from 16-hydroxytotarol. Podototarin (IV, R  CH3) has been prepared by a one-step enzymatic coupling of (+)-totarol and the coupling reaction extended to the preparation of the lithium aluminum hydride reduction

  从心材Macrophyllic酸罗汉松已被证明是bisditerpenoid二羧酸（我，- [R  ħ）有关podototarin，其二-O-甲基二甲基酯等合成从16羟基桃拓酚。Podototarin（IV，- [R  CH 3）已经被制备（+）的一步骤酶促偶联-桃拓酚以及在偶联反应扩展macrophyllic酸二甲酯的氢化铝锂还原产物的制备。
• Laccase-Mediated Oxidation of Totarol
  作者：Sandile Ncanana、Lara Baratto、Lucia Roncaglia、Sergio Riva、Stephanie G Burton

  DOI：10.1002/adsc.200700005

  日期：2007.6.4

  phenolic compound totarol were synthesized using the phenol oxidase enzyme laccase, obtained from Trametes pusbescens, in organic solvent medium. Two dimeric products, linked either by carbon-carbon or by carbon-oxygen bonds, were isolated and characterized. The effect of changes in various parameters such as solvent, temperature, pH and buffer concentration on the conversion of totarol by laccase was

  在这项研究中，使用从Trametes pusbescens获得的苯酚氧化酶酶漆酶，在有机溶剂介质中合成了具有生物活性的酚类化合物totarol的新型二聚体。分离并表征了通过碳-碳键或通过碳-氧键连接的两个二聚体产物。研究了溶剂，温度，pH和缓冲液浓度等各种参数的变化对漆酶转化甲苯酚的影响。特别地，发现有机溶剂的性质影响所得产物的性质和比例。
• Chemoenzymatic synthesis of (+)-totarol, (+)-podototarin, (+)-sempervirol, and (+)-jolkinolides E and D
  作者：Takahiro Miyake、Hideo Kigoshi、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2007.11.024

  日期：2007.12

  The enzymatic resolution products [(1R,4aR,8aR)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal (8aR)-7 (98% ee) and acetate of (IS,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal} (8aS)-9 (>99% ee)] obtained by the lipase-catalyzed enantioselective acetylation of (+/-)-7 in the presence of vinyl acetate as an acyl donor were converted to the alpha,beta-unsaturated ketones (8aR)-6 and (8aS)-6, respectively. Concise syntheses of (+)-totarol 1, (+)-podototarin 2 and (+)-sempervirol 3 were achieved based on Michael reactions between (8aS)-6 and the appropriate P-keto ester followed by aldol condensation. The first chiral syntheses of (+)-jolkinolides E 4 and D 5 were achieved from (5R,10R,12R)-12-hydroxypodocarpa-8(14)-en-13-one 15 derived from (8aR)-6. (c) 2007 Elsevier Ltd. All rights reserved.