(+/-)-Drim-9(11)-en-8α-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-Drim-9(11)-en-8α-ol
• 英文别名: (2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-methylidene-3,4,4a,6,7,8-hexahydronaphthalen-2-ol
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: SAJLLZGTTHMQBE-NWANDNLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-Drim-9(11)-en-8α-ol 在 硼烷四氢呋喃络合物 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 25.0h， 生成 (-)-补身醇
  参考文献：
  名称：

  First Enantiospecific Synthesis of the Antitumor Marine Sponge Metabolite (−)-15-Oxopuupehenol from (−)-Sclareol

  摘要：

  [GRAPHICS]A new route toward puupehenone-related bioactive metabolites from (-)-sclareol, based on the palladium(II)-mediated diastereoselective cyclization of a drimenylphenol, is described. Utilizing this, the first enantiospecific synthesis of the antitumor and antimalarial (-)-15-oxopuupehenol, together with improved syntheses of (+)-puupehenone, (+)-puupehedione, and (+)-15-cyanopuupehenone, were accomplished.

  DOI：

  10.1021/ol047332j
• 作为产物：
  描述：

  (2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol 在 氢氧化钾 、 copper(l) iodide 、 重铬酸吡啶 、 二甲基硫 、 三氟化硼乙醚 、 亚甲兰 、 二异丁基氢化铝 、 臭氧 、 一水合肼 、 magnesium 、 CrO₃-3.5-dimethylpyrazole 、 sodium iodide 、 锌 作用下， 以 乙二醇二甲醚 、 甲苯 、 苯 为溶剂， 反应 52.83h， 生成 (+/-)-Drim-9(11)-en-8α-ol
  参考文献：
  名称：

  Shishido, Kozo; Omodani, Tomoki; Shibuya, Masayuki, Journal of the Chemical Society. Perkin transactions I, 1991, # 9, p. 2285 - 2287

  摘要：

  DOI：

文献信息

• Modular Synthesis of Drimane Meroterpenoids Leveraging Decarboxylative Borylation and Suzuki Coupling
  作者：Xia Wang、Shasha Zhang、Pengcheng Cui、Shengkun Li

  DOI：10.1021/acs.orglett.0c03294

  日期：2020.11.6

  conspicuous challenge. A new paradigm merging decarboxylative borylation and Suzuki coupling was developed as a powerful platform. Key features include the mild conditions, good chemoselectivity, operational facility, scalability, and easy availability of the coupling partners. This practical strategy enables the expedient formal synthesis of a large number of natural products and rapid generation of analogues

  在治疗上重要的探针的发现中，地烷类金属萜类化合物已引起越来越多的关注，而落后的合成可及性是一个显着的挑战。结合脱羧硼化和Suzuki偶联的新范式被开发为强大的平台。主要功能包括温和的条件，良好的化学选择性，操作设施，可扩展性以及耦合伙伴的简便可用性。这种实用的策略使大量天然产物的便捷形式合成和快速生成类似物成为可能。
• Synthesis of (+)-drim-9(11)-en-8 -ol from sclareol
  作者：P. F. Vlad、A. N. Aryku、A. G. Chokyrlan

  DOI：10.1023/b:rucb.0000030822.72251.ea

  日期：2004.2

  A drimane-type sesquiterpenoid, (+)-drim-9(11)-en-8α-ol, was synthesized from sclareol in four steps. The ozonolysis product of sclareol diacetate reacts with Cu(OAc)2·H2O to give 8α-acetoxy-14,15-bisnorlabdan-13-one. Photolysis of this compound followed by alkaline hydrolysis results in the target compound belonging to the normal steric series. (+)-Drim-9(11)-en-8α-ol acetate is highly unstable and

  一种 drimane 型倍半萜类化合物 (+)-drim-9(11​​)-en-8α-ol，由香紫苏分四步合成。香紫苏醇二乙酸酯的臭氧分解产物与 Cu(OAc)2·H2O 反应生成 8α-乙酰氧基-14,15-bisnorlabdan-13-one。该化合物的光解和碱水解产生属于正常空间系列的目标化合物。(+)-Drim-9(11​​)-en-8α-ol 醋酸盐非常不稳定，在 SiO2 色谱过程中会分解。
• Synthesis of Drim-9(11)-en-8α- and -8β-ols from Drimenol
  作者：K. I. Kuchkova、A. N. Aryku、I. P. Dragalin、P. F. Vlad

  DOI：10.1007/s10600-005-0109-8

  日期：2005.3

  Drim-9(11)-en-8α-ol and drim-9(11)-en-8β-ol were synthesized in six steps from drimenol. Drimenol was oxidized by P2O5 and DMSO to drimenal, which isomerized with p-TsOH into isodrimenal. Isodrimenal was reduced by NaBH4 into isodrimenol, epoxidation of which by m-CPBA gave a mixture (3.4:1) of α- and β-epoxyisodrimenols. These reacted with tosyl chloride in Py to give a mixture of α- and β-epoxyisodrimenol tosylates. Treatment of the tosylate mixture with KI and then Ph3P produced a mixture of drim-9(11)-en-8α- and -8β-ols that was separated chromatographically. The overall yield was ∼26%.

  Drim-9(11)-en-8α-醇和drim-9(11)-en-8β-醇是通过六个步骤从drimenol合成的。drimenol先由P2O5和DMSO氧化为drimenal，随后在p-TsOH的催化下异构化为isodrimenal。isodrimenal再通过NaBH4还原为isodrimenol，接着用m-CPBA进行环氧化，得到混合物(3.4:1)的α-和β-环氧isodrimenol。这些化合物与吡啶中的tosyl氯反应，生成α-和β-环氧isodrimenol tosylates的混合物。将该tosylate混合物与KI及Ph3P处理后，分离得到drim-9(11)-en-8α-和-8β-醇的混合物，通过色谱分离。这一系列反应的总体产率约为26%。
• Regioselective 1,2-Diol Rearrangement by Controlling the Loading of BF₃·Et₂O and Its Application to the Synthesis of Related Nor-Sesquiterene- and Sesquiterene-Type Marine Natural Products
  作者：Jun-Li Wang、Hui-Jing Li、Hong-Shuang Wang、Yan-Chao Wu

  DOI：10.1021/acs.orglett.7b01679

  日期：2017.7.21

  achieved by controlling the loading of BF3·Et2O. Its applicability is showcased by the divergent synthesis of austrodoral, austrodoric acid, and 8-epi-11-nordriman-9-one, as well as a formal synthesis of siphonodictyal B and liphagal. A new light is shed on piancol-type rearrangements that will be useful in diversity-oriented synthesis of related natural products.

  通过控制BF 3 ·Et 2 O的负载，实现了1,2-二醇的区域控制重排。其适用性通过奥氏体，奥氏多酸和8- Epi -11-nordriman-9-one的发散合成得以展示。，以及虹吸管B和脂蛋白的正式合成。有关piancol类型重排的新见解，将在相关天然产物的面向多样性的合成中有用。
• Synthesis of Pelorol and Its Analogs and Their Inhibitory Effects on Phosphatidylinositol 3-Kinase
  作者：Yongjie Luo、Huixuan Chen、Jiang Weng、Gui Lu

  DOI：10.3390/md14060118

  日期：——

  important sources of new lead compounds. Pelorol is a natural product isolated from marine organisms that possesses a novel structure with high bioactivity. In this paper, the synthesis of pelorol has been completed, and the synthesis of some intermediates has been optimized and scaled up. Five pelorol analogs have also been prepared. Preliminary biological activity testing demonstrated that compounds 5

  海洋生物中有许多具有新颖结构和独特生理功能的生物活性物质。这些物质是新的铅化合物的重要来源。Pelorol是从海洋生物中分离出来的天然产物，具有一种具有高生物活性的新型结构。本文已完成了对邻苯三酚的合成，并对某些中间体的合成进行了优化和扩大规模。还制备了五种波洛洛类似物。初步的生物活性测试表明，化合物5和6可能是潜在的癌症治疗先导化合物。