Teuscorolide | 41759-79-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: Teuscorolide
• 英文别名: (5'S,8S,9R,10R)-5'-(furan-3-yl)-10-methylspiro[2-oxatricyclo[6.3.1.04,12]dodeca-1(11),4(12)-diene-9,3'-oxolane]-2',3-dione
• CAS: 41759-79-9
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: CZNJEOYBTZXDQG-FVVULKDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 Teuscorolide 在 potassium carbonate 作用下， 反应 2.0h， 以84%的产率得到5-(furan-3-yl)-8a'-methoxy-7'-methyl-3',4,5,5',5a',7',8',8a'-octahydro-2H-spiro[furan-3,6'-naphtho[1,8-bc]furan]-2,2'(4'H)-dione
  参考文献：
  名称：

  Transformation of neoclerodane diterpenoids into 19-norneoclerodane derivatives

  摘要：

  The neoclerodane diterpenoid eriocephalin (1) was transformed into its 19-nor derivatives 3 and 4 by reaction with potassium tert-butoxide in THF, whereas with the same treatment compound 6 yielded only the transacetylation derivative 7. These results indicated that 19-acetoxy-4-alpha,18-epoxy-7-alpha-hydroxy-6-oxoneoclerodane derivatives are transformed into the corresponding 19-nor compounds in a retroaldol reaction by loss of the C-19 carbon as formaldehyde followed by opening of the oxirane ring and intramolecular attack by a C-18 alkoxide on the carbonyl C-6 carbon atom, giving the allylic hemiacetal 3, which is easily dehydrated to the furanic derivative 4. Compound 4 was transformed into the alpha,beta-unsaturated gamma,delta-enol gamma-lactone 8 by an oxidation reaction with atomspheric oxygen in chloroform solution. Alternatively, it gave the alpha,beta-unsaturated gamma-lactone 11 under acid catalysis. These reactions allowed the partial syntheses of the naturally occurring diterpenoids teuscorolide (9) and teucvin (12) and are of interest for chemical transformations of substances of this kind.

  DOI：

  10.1021/jo00023a027
• 作为产物：
  描述：

  5-(furan-3-yl)-7'-methyl-2'-oxo-2',3',4,4',5,5',5a',7'-octahydro-2H-spiro[furan-3,6'-naphtho[1,8-bc]furan]-2-yl acetate 在 chromium trioxide-pyridine complex 、 硫酸 作用下， 生成 Teuscorolide
  参考文献：
  名称：

  Transformation of neoclerodane diterpenoids into 19-norneoclerodane derivatives

  摘要：

  The neoclerodane diterpenoid eriocephalin (1) was transformed into its 19-nor derivatives 3 and 4 by reaction with potassium tert-butoxide in THF, whereas with the same treatment compound 6 yielded only the transacetylation derivative 7. These results indicated that 19-acetoxy-4-alpha,18-epoxy-7-alpha-hydroxy-6-oxoneoclerodane derivatives are transformed into the corresponding 19-nor compounds in a retroaldol reaction by loss of the C-19 carbon as formaldehyde followed by opening of the oxirane ring and intramolecular attack by a C-18 alkoxide on the carbonyl C-6 carbon atom, giving the allylic hemiacetal 3, which is easily dehydrated to the furanic derivative 4. Compound 4 was transformed into the alpha,beta-unsaturated gamma,delta-enol gamma-lactone 8 by an oxidation reaction with atomspheric oxygen in chloroform solution. Alternatively, it gave the alpha,beta-unsaturated gamma-lactone 11 under acid catalysis. These reactions allowed the partial syntheses of the naturally occurring diterpenoids teuscorolide (9) and teucvin (12) and are of interest for chemical transformations of substances of this kind.

  DOI：

  10.1021/jo00023a027

文献信息

• Total syntheses of (±)-montanin A and (±)-teuscorolide
  作者：I-Chia Chen、Yen-Ku Wu、Hsing-Jang Liu、Jiang-Liang Zhu

  DOI：10.1039/b807218c

  日期：——

  The first total syntheses of (±)-montanin A and (±)-teuscorolide have been achieved from an advanced precursor previously developed via a Diels–Alder strategy; in the synthetic sequence, the synthesis of montanin A was first accomplished in 8 steps, from which teuscorolide was readily achieved in 2 steps by using a novel furan oxidative cyclization–retro-cyclization process as a key operation.

  (±)-montanin A 和 (±)-teuscorolide 的首次全合成是由先前通过 Diels-Alder 策略开发的先进前体实现的；在合成过程中，首先通过8步完成了montanin A的合成，然后以新型呋喃氧化环化-逆环化工艺为关键操作，通过2步轻松合成了teuscorolide。
• Diterpenoids from Teucrium scorodonia, three neo-clerodane derivatives
  作者：Jose L. Marco、Benjamín Rodríguez、Giuseppe Savona、Franco Piozzi

  DOI：10.1016/0031-9422(82)85258-8

  日期：1982.1

  Abstract From the aerial parts of Teucrium scorodonia the previously known diterpenoid teupolin I and the flavone luteolin have been isolated. In addition, three new neo-clerodane derivatives have also been obtained from the same source. The structures of these new natural diterpenoids have been established by chemical and spectroscopic means and by correlation with known products.

  摘要 从 Teucrium scorodonia 的地上部分已经分离出先前已知的二萜类 teupolin I 和黄酮木犀草素。此外，还从同一来源获得了三种新的新克罗丹衍生物。这些新的天然二萜类化合物的结构已通过化学和光谱方法以及与已知产品的相关性确定。
• Efficient Installation and Elaboration of C4-C6 fused Furan Moiety in the Total Synthesis of Teucrium Clerodane Diterpenoids
  作者：Jia-Liang Zhu、Hsing-Jang Liu、Yen-Ku Wu、I-Chia Chen

  DOI：10.3987/com-14-13045

  日期：——

  We previously reported the total synthesis of several Teucrium clerodane diterpenoids including teucvin (1), 12-epi-teucvin (2), montanin A (3) and teuscorolide (4) in a unified Diels-Alder approach. A full account for the tactical installation of the C4-C6 furan ring. of 3 from an alpha,beta-unsaturated lactone moiety, and the elaboration of the resulting furan unit into alpha,beta-unsaturated gamma-hydroxyl lactone for preparing 4 is discussed herein. In addition, the transformation of 3 and its 12-epimer into 1 and 2 by the air-mediated furan oxidation reaction is described.
• Transformation of neoclerodane diterpenoids into 19-norneoclerodane derivatives
  作者：Gema Dominguez、Maria C. De la Torre、Benjamin Rodriguez

  DOI：10.1021/jo00023a027

  日期：1991.11

  The neoclerodane diterpenoid eriocephalin (1) was transformed into its 19-nor derivatives 3 and 4 by reaction with potassium tert-butoxide in THF, whereas with the same treatment compound 6 yielded only the transacetylation derivative 7. These results indicated that 19-acetoxy-4-alpha,18-epoxy-7-alpha-hydroxy-6-oxoneoclerodane derivatives are transformed into the corresponding 19-nor compounds in a retroaldol reaction by loss of the C-19 carbon as formaldehyde followed by opening of the oxirane ring and intramolecular attack by a C-18 alkoxide on the carbonyl C-6 carbon atom, giving the allylic hemiacetal 3, which is easily dehydrated to the furanic derivative 4. Compound 4 was transformed into the alpha,beta-unsaturated gamma,delta-enol gamma-lactone 8 by an oxidation reaction with atomspheric oxygen in chloroform solution. Alternatively, it gave the alpha,beta-unsaturated gamma-lactone 11 under acid catalysis. These reactions allowed the partial syntheses of the naturally occurring diterpenoids teuscorolide (9) and teucvin (12) and are of interest for chemical transformations of substances of this kind.