8S-13,14,15,16-tetranorlabdan-12-al | 199438-57-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8S-13,14,15,16-tetranorlabdan-12-al
• 英文别名: 2-[(1S,2S,4aS,8aR)-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]acetaldehyde
• CAS: 199438-57-8
• 化学式: C₁₆H₂₈O
• 分子量: 236.398
• InChiKey: MJUCEVOCSCWXCJ-RZLSGREXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8S-13,14,15,16-tetranorlabdan-12-al 在 正丁基锂 、 二甲基硫 、 sodium hydride 、 对甲苯磺酸 、 臭氧 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 23.25h， 生成 8S-1,2-di-O-benzyl-3-(9'-drimen-11'-yl)-4-O-methylbenzenetriol
  参考文献：
  名称：

  Enantiospecific Synthesis of Wiedendiol-B from (−)-Sclareol and (+)-cis-Abienol

  摘要：

  The first enantiospecific synthesis of the cholesteryl ester transfer protein (CETP) inhibitor wiedendiol-B (1) is described. The drimanic synthon was prepared from (-)-sclareol (4) and (+)-cis-abienol (13) by two alternative routes. The key steps of the reaction sequences are the chemo-and diastereoselective hydrogenation of the C-8-C-9 double bond of enal 6 and the stereoselective cationic hydrogenation of the hydroxyl group of 13, respectively, and the selective reduction of benzyl groups of 15. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10119-8
• 作为产物：
  描述：

  (+)-顺式-枞醇 在 二甲基硫 、 氧气 、 sodium cyanoborohydride 、 臭氧 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 8S-13,14,15,16-tetranorlabdan-12-al
  参考文献：
  名称：

  Synthesis of wiedendiol-A and wiedendiol-B from labdane diterpenes

  摘要：

  Two efficient enantiospecific syntheses of wiedendiol-A (1) from (-)-sclareol (7), via 11-bromo-8-drimene (11) and 8-drimen-11-al (3), are reported. The first enantiospecific synthesis of wiedendiol-B (2), via 8S,9S-driman-11-al (26), by two alternative routes starting from 7 and (+)-cis-abienol (8) is also described. 21 prepared from protocatechualdehyde (17) was used as aromatic synthon for preparing 1 and 2. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00235-x

文献信息

• Enantioselective Access to (−)-<i>Ambrox</i>^®Starting from<i>β</i>-Farnesene
  作者：Christian Chapuis

  DOI：10.1002/hlca.201300286

  日期：2014.2

  Starting from inexpensive (E)‐β‐farnesene (1), an eight‐step enantioselective synthesis of the olfactively precious Ambrox® ((−)‐2a) has been performed. The crucial step is the catalytic asymmetric isomerization of (2E,6E)‐N,N‐diethylfarnesylamine (3) to the corresponding enamine (−)‐(R,E)‐4a, applying Takasago's well‐known industrial methodology. The resulting dihydrofarnesal ((+)‐(R)‐5) (90% yield

  从廉价的（起始ë - ）β法呢烯（1），一个八步骤对映选择性的嗅觉珍贵的合成艾姆罗克斯®（ - ） - （2a中已经执行）。关键步骤是应用高砂的著名工业方法，将（2 E，6 E）‐ N，N-二乙基法呢胺（3）催化成对应的烯胺（−）‐（R，E）‐4a的催化不对称异构化。产生的二氢肾上腺素（（+] ‐（R）‐5）（90％产率，96％ee）的，后获得原位水解（AcOH中，H 2 O），催化的SnCl下然后环化4的条件下，通过） - - （其相应未报告的烯醇乙酸酯（- [R ） - 4b中，以提供反癸醛（+）- 6a。随后的转化提供了双环酮（−）‐ 8a和不饱和腈（+）‐ 11，它们均被报告为获得（−）‐ 2a的中间体。
• Adinolfi,M. et al., Gazzetta Chimica Italiana, 1968, vol. 98, p. 107 - 121
  作者：Adinolfi,M. et al.

  DOI：——

  日期：——
• Enantiospecific Synthesis of Wiedendiol-B from (−)-Sclareol and (+)-cis-Abienol
  作者：Alejandro F. Barrero、Enrique J. Alvarez-Manzaneda、Rachid Chahboun

  DOI：10.1016/s0040-4039(97)10119-8

  日期：1997.11

  The first enantiospecific synthesis of the cholesteryl ester transfer protein (CETP) inhibitor wiedendiol-B (1) is described. The drimanic synthon was prepared from (-)-sclareol (4) and (+)-cis-abienol (13) by two alternative routes. The key steps of the reaction sequences are the chemo-and diastereoselective hydrogenation of the C-8-C-9 double bond of enal 6 and the stereoselective cationic hydrogenation of the hydroxyl group of 13, respectively, and the selective reduction of benzyl groups of 15. (C) 1997 Elsevier Science Ltd.
• Synthesis of wiedendiol-A and wiedendiol-B from labdane diterpenes
  作者：Alejandro F. Barrero、Enrique J. Alvarez-Manzaneda、Rachid Chahboun

  DOI：10.1016/s0040-4020(98)00235-x

  日期：1998.5

  Two efficient enantiospecific syntheses of wiedendiol-A (1) from (-)-sclareol (7), via 11-bromo-8-drimene (11) and 8-drimen-11-al (3), are reported. The first enantiospecific synthesis of wiedendiol-B (2), via 8S,9S-driman-11-al (26), by two alternative routes starting from 7 and (+)-cis-abienol (8) is also described. 21 prepared from protocatechualdehyde (17) was used as aromatic synthon for preparing 1 and 2. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.