8α-acetoxydriman-11-al | 165816-95-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 8α-acetoxydriman-11-al
• 英文别名: [(1R,2R,4aS,8aS)-1-formyl-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl] acetate
• CAS: 165816-95-5
• 化学式: C₁₇H₂₈O₃
• 分子量: 280.408
• InChiKey: DXAHQNIWIBZTDS-HDEZJCGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8α-acetoxydriman-11-al 在 palladium on activated charcoal 2,3,5-三甲基吡啶 、 氢气 、 三溴化磷 作用下， 以 甲醇 、 乙醚 、 乙酸乙酯 为溶剂， 反应 4.5h， 生成 1,2-di-O-benzyl-3-(8'-drimen-11'-yl)-4-O-methylbenzenetriol
  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
• 作为产物：
  描述：

  8α-acetoxy-12-t-butyldimethylsilyloxy-13,14,15,16-tetranorlabd-11E/Z-ene 在 二甲基硫 、 臭氧 作用下， 生成 8α-acetoxydriman-11-al
  参考文献：
  名称：

  Synthesis of biologically active drimanes and homodrimanes from (−)-sclareol

  摘要：

  Three drimanes, polygodial (2), albicanyl acerate (3) and 7-oxo-8,12-drimen-11-al (5), and two homodrimanes, 13,14,15,16-tetranorlabd-7-en-12,17-dial (6) and 7-oxo-13,14,15,16-tetranorlabd-8(17)-en-12-al (7), were synthesized from (-)-sclareol (1), and their antifeedant, antitumor and antimicrobial properties tested. In mast cases, 6 and 7 were found to be more active than 2.

  DOI：

  10.1016/0040-4020(95)00370-n

文献信息

• Synthesis and antitumor activity of puupehedione and related compounds
  作者：Alejandro F. Barrero、Enrique J. Alvarez-Manzaneda、Rachid Chahboun、M. Cortés、V. Armstrong

  DOI：10.1016/s0040-4020(99)00992-8

  日期：1999.12

  The first enantiospecific synthesis of bioactive marine puupehedione (2) and related compounds from (−)-sclareol (11) is reported. The antitumor activity of these compounds was assayed and compared with that of the natural products.

  据报道，首次从（-）-香紫苏醇（11）合成了生物活性海洋puupehedione（2）和相关化合物的对映体。测定这些化合物的抗肿瘤活性并将其与天然产物的抗肿瘤活性进行比较。
• Synthesis and antitumoral activities of marine ent-chromazonarol and related compounds
  作者：Alejandro F. Barrero、Enrique J. Alvarez-Manzaneda、M.Mar Herrador、Rachid Chahboun、P. Galera

  DOI：10.1016/s0960-894x(99)00382-0

  日期：1999.8

  Efficient syntheses of ent-isozonarol (6a), ent-isozonarone (7a) and ent-chromazonarol (8) from (-)-sclareol (12) are described. 6a and 7a show a significative antitumoral activity. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Absolute stereochemistry of natural sesquiterpenoid diacylglycerols
  作者：Nicon Ungur、Margherita Gavagnin、Angelo Fontana、Guido Cimino

  DOI：10.1016/s0957-4166(99)00119-6

  日期：1999.4

  The absolute stereochemistry of farnesic and drimenic glyceryl esters la-le and 2a-2b, previously isolated from marine dorid nudibranchs, has been established by their synthesis. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.