Synthetic Studies on Biologically Active Poly-Functionalized Carbazoles

生物活性多官能咔唑的合成研究

• 批准号: 07672303
• 负责人: HIBINO Satoshi
• 金额: $ 0.77万
• 依托单位: Fukuyama University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 1995
• 资助国家: 日本
• 起止时间: 1995 至 1996
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-07672303/
• 关键词: carbazole alkaloid; carazostatin; hyellazole; carbazoquinocins B-F; synthesis; electrocyclic reaction; allene intermediate; oxazolocarbazole

1. The free radical scavenger carazostatin and the marine alkaloid hyellazole have been synthesized by a new type of allene-mediated electrocyclic reaction involving the indole 2,3-bond as a key step.2. New tetracyclic oxazolo [4,5-c] carbazole and oxazolo [5,4-c] carbazole ring systems as functionalized precursors to antioxidative antiostatins (A_<1-4> and B_<2-5>) and carbazoquinocins (A-F) were synthesized.3. A new benzo-annelation method based on the allene-mediated electrocyclic reaction of 2,3-functionalized indoles provides an effective route to the highly-functionalized carbazole ring, and the total syntheses of carazostatin, hyellazole and carbazoquinocins B to F have been completed. Moreover, the first total syntheses of carbazoquinocins B,C,E and F were demonstrated.

1.以吲哚2，3-键为关键步骤，通过一种新型的烯丙基电环反应，合成了自由基清除剂卡拉索他汀和海洋生物碱海拉唑。合成了四环恶唑并[4，5-c]咔唑和恶唑并[5，4-c]咔唑作为抗氧化剂(A_&lt；1-4&gt；和B_&lt；2-5&gt；)和咔唑并喹啉(A-F)的官能化前驱体。基于2，3-官能化吲哚的烯丙基电环反应的苯并芳化新方法为合成高官能化的咔唑环提供了一条有效的途径，并完成了卡拉佐菌素、海拉唑和卡巴喹菌素B到F的全合成。此外，还首次实现了碳偶氮喹菌素B、C、E和F的全合成。

项目成果

日比野俐: "Total Syntheses of Carazostatin, Hyellazole and Carbazoquinocins B to F" The Journal of Organic Chemistry. 62(in press). (1997)

Takeru Hibino：“Carazostatin、Hyellazo 和 Carbaquinocins B 至 F 的全合成”有机化学杂志 62（出版中）。

日比野俐: "Synthesis of New Tetracyclic Oxazolocarbazoles as Functionalized Precursors to Antioxidative Agents, Antiostatins" Heterocycles. 43. 1847-1854 (1996)

Hibino Takeru：“作为抗氧化剂、抗抑素的功能化前体的新型四环恶唑并咔唑的合成”杂环。 43。1847-1854 (1996)

日比野俐他: "Synthesis of New Tetracyclic Oxazolocarbazoles as Functionalized Precursors to Antioxidative Agents,Antiostatins and Carbazoquinocis" Heterocycles. 43,9. 1847-1854 (1996)

Hibino Masaru 等人：“新四环恶唑并咔唑作为抗氧化剂、抗抑菌素和卡巴喹诺的功能化前体的合成”杂环43,9 (1996)。

Tominari Choshi, Hiroyuki Fujimoto, Eiichi Sugino, and Satoshi Hibino: "Synthesis of New Tetracyclic Oxazolocarbazoles as Functionalized Precursors to Antioxidative Agents, Antiostatins and Carbazoquinocins" Heterocycles. Vol.43 No.9. 1847-1854 (1996)

Tominari Choshi、Hiroyuki Fujimoto、Eiichi Sugino 和 Satoshi Hibino：“作为抗氧化剂、抗抑素和卡巴喹啉的功能化前体的新型四环恶唑并咔唑的合成”杂环。

日比野俐他: "Total Syntheses of Carazostatin,Hyellazole and Carbazoquinocins B to F" J.Org.Chem.(in press). (1997)

Hibino Masaru 等人：“Carazostatin、Hyellazo 和 Carbaquinocins B 至 F 的全合成”J.Org.Chem.（出版中）。