(+)-cyclocapitelline | 271249-84-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (+)-cyclocapitelline
• 英文别名: 2-[(2R,5R)-5-methyl-5-(9H-pyrido[3,4-b]indol-1-ylmethyl)oxolan-2-yl]propan-2-ol
• CAS: 271249-84-4
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: BFOYOQPBKKWMJY-YLJYHZDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  58.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-cyclocapitelline 在 sodium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 2.0h， 生成 chrysotricine
  参考文献：
  名称：

  The total synthesis of chrysotricine

  摘要：

  Geraniol was converted, using Sharpless oxidations as key steps, into the chiral tuans-tri-substituted tetrahydrofuran 10, from which chrysotricine was synthesized in 16 steps (1.1% overall yield). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00146-5
• 作为产物：
  描述：

  Methanesulfonic acid 2-[(2R,5R)-5-(2-benzyloxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-2-hydroxy-propyl ester 在 palladium on activated charcoal palladium on activated charcoal 、 lithium aluminium tetrahydride 、 草酰氯 、 氢气 、 二甲基亚砜 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (+)-cyclocapitelline
  参考文献：
  名称：

  The total synthesis of chrysotricine

  摘要：

  Geraniol was converted, using Sharpless oxidations as key steps, into the chiral tuans-tri-substituted tetrahydrofuran 10, from which chrysotricine was synthesized in 16 steps (1.1% overall yield). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00146-5

文献信息

• Oxidative cyclization of tertiary pentenol derivatives forming 2,5,5-trisubstituted THF rings and the total synthesis of cyclocapitelline
  作者：Geoffrey A. Phillips、Cory Palmer、Andrew C. Stevens、Mathew L. Piotrowski、Daryl S.R. Dekruyf、Brian L. Pagenkopf

  DOI：10.1016/j.tetlet.2015.09.064

  日期：2015.10

  The synthesis of 2,5,5-trisubstituted tetrahydrofuran rings was accomplished via the Mukaiyama aerobic oxidative cyclization of tertiary 5-pentenols employing the Co(nmp)2 catalyst. A variety of THFs were formed in moderate to good yield and diastereoselectivity. The method developed herein was successfully applied to an enantioselective total synthesis of cyclocapitelline.

  2,5,5-三取代的四氢呋喃环的合成是通过使用Co（nmp）2催化剂对5-戊烯叔叔醇进行Mukaiyama有氧氧化环化来完成的。以中等至良好的产率和非对映选择性形成了各种THF。本文开发的方法已成功地应用于环己内酯的对映选择性全合成。
• A protecting-group-free synthesis of arbusculone, andirolactone, pinnatolide, ipomolactone, cyclocapitelline and isocyclocapitelline
  作者：Srinivas Gajula、Madasu Madhu、Suresh Kumar Chintakrinda、J.S. Yadav、Debendra K. Mohapatra

  DOI：10.1016/j.tetlet.2018.10.024

  日期：2018.11

  A general approach for a collective synthesis of natural products containing substituted THF ring is described. In this paper, Arbusculone, a small molecule natural product accomplished using a short route, is used as the key intermediate to achieve the total synthesis of Andirolactone, Pinnatolide, Ipomolactone, Cyclocapitelline, Isocyclocapitelline and their two isomers in less than ten steps. The

  描述了用于集体合成含有取代的THF环的天然产物的一般方法。在本文中，使用短路径完成的小分子天然产物Arbusculone被用作关键中间体，可在不到十个步骤的情况下完成Andirolactone，Pinnatolide，Ipomolactone，Cyclocapitelline，Isocyclocapitelline及其两个异构体的全合成。目前的工作着重强调了无保护基团的全部合成方法，以及从市售廉价原料中获得这些天然产物的最短途径。
• The total synthesis of chrysotricine
  作者：Jing-Xin Zhang、Guang-Xing Wang、Ping Xie、Shu-Feng Chen、Xiao-Tian Liang

  DOI：10.1016/s0040-4039(00)00146-5

  日期：2000.3

  Geraniol was converted, using Sharpless oxidations as key steps, into the chiral tuans-tri-substituted tetrahydrofuran 10, from which chrysotricine was synthesized in 16 steps (1.1% overall yield). (C) 2000 Elsevier Science Ltd. All rights reserved.