tubingensin A

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: tubingensin A
• 英文别名: (16S,17R,20S,21R)-16,17-dimethyl-21-(4-methylpent-3-enyl)-10-azapentacyclo[11.8.0.03,11.04,9.016,21]henicosa-1,3(11),4,6,8,12-hexaen-20-ol
• 化学式: C₂₈H₃₅NO
• 分子量: 401.592
• InChiKey: BWCQRIGHZTXFEA-AIERRPMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-benzenesulfonyl-tubingensin A 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 以6.8 mg的产率得到tubingensin A
  参考文献：
  名称：

  Total Syntheses of Anominine and Tubingensin A

  摘要：

  A divergent strategy for the total syntheses of the indole terpenoid anominine (1) and its natural congener tubingensin A (2) has been developed. The common intermediate 11 bearing all of the required stereogenic centers for both natural products was first assembled by employing a Ueno-Stork radical cyclization and a Sc(OTf)(3)-mediated Mukaiyama aldol reaction to form the key C-C bonds in a stereocontrolled manner. The route to anominine features a radical deoxygenation followed by an efficient side-chain installation, while the path to tubingensin A exploits a CuOTf-promoted 6 pi-electrocyclization/aromatization sequence to forge the central region of the pentacyclic scaffold.

  DOI：

  10.1021/ja302765m

文献信息

• Concise Enantiospecific Total Synthesis of Tubingensin A
  作者：Adam E. Goetz、Amanda L. Silberstein、Michael A. Corsello、Neil K. Garg

  DOI：10.1021/ja501142e

  日期：2014.2.26

  We report the enantiospecific total synthesis of (+)-tubingensin A. Our synthesis features an aryne cyclization to efficiently introduce the vicinal quaternary stereocenters of the natural product and proceeds in only nine steps (longest linear sequence) from known compounds.

  我们报告了 (+)-tubingensin A 的对映特异性全合成。我们的合成特征是芳炔环化，以有效地引入天然产物的邻位四元立体中心，并且从已知化合物仅以九个步骤（最长的线性序列）进行。
• Dihydrocarbazole Alkaloids from <i>Aspergillus </i><i>t</i><i>ubingensis</i>
  作者：Heather L. Sings、Guy H. Harris、Anne W. Dombrowski

  DOI：10.1021/np000613p

  日期：2001.6.1

  Investigation of the fungus Aspergillus tubingensis has led to the isolation and identification of two dihydrocarbazole-containing compounds (1 and 2). Details of the purification and structure elucidation of 1 and 2 are described. This is the first known report of dihydrocarbazole-containing compounds to be isolated from a living system.

  对真菌曲霉曲霉的研究导致了两种含二氢咔唑化合物（1和2）的分离和鉴定。描述了1和2的纯化和结构阐明的细节。这是从生物系统中分离出的含二氢咔唑化合物的第一个已知报告。