Studies on benzo [c] phenanthridine alkaloid using novel palladium reagents

使用新型钯试剂研究苯并[c]菲啶生物碱

• 批准号: 09672144
• 负责人: HARAYAMA Takashi
• 金额: $ 1.86万
• 依托单位: Okayama University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 1997
• 资助国家: 日本
• 起止时间: 1997 至 1998
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-09672144/
• 关键词: palladium reagent; chelerythrine; nitidine; benzo [c] phenanthridine; benzo [d] naphthopyranone; biaryl coupling reaction; ベンゾ[C]フェナンスリジン

1) Development of general synthetic method for benzo[c]phenanthridine alkaloid using novel palladium reagentsA novel palladium reagent prepared from equimolar Pd(OAc)_2, DPPP, and Bu3P was useful for the internal biaryl coupling reaction of not only triflate-amide but also halo-amide as leaving group. By using this novel Pd reagent, benzo[c]phenanthridine alkaloids, chelerythrine and nitidine were synthesized in good yields.2) Synthetic studies on benzo[d]naphthopyranonesBenzo[d]naphthopyranones, arnottin I, was synthesized by using typical Heck* s reaction conditions.3) Synthetic studies on phenanthridine alkaloidsPhenanthridine alkaloid, trisphaeridine, was synthesized via biaryl coupling reaction using palladium reagent.4) Mechanistic aspect of novel Palladium reagent [Pd(OAc)_2-PPP-Bu_3P]It was found out that molar ratio of Pd phosphine = 1 : 3 is essentially necessary for biaryl coupling reaction

以等摩尔Pd(OAc)_2、DPPP和Bu3P为原料合成了一种新的钯试剂，不仅可用于三氟酰胺的内部联芳基偶联反应，还可用于卤代酰胺的离基反应。2)采用典型的Heck*S反应条件合成了benzo[d]naphthopyranonesBenzo[d]naphthopyranones，阿诺替丁I；3)菲生物碱的合成研究用钯试剂通过联芳基偶联反应合成了菲生物碱三氢菲；4)新型钯试剂[Pd(OAc)_2-ppp-Bu3P]的反应机理研究发现，钯膦的摩尔比为1：3是联芳偶联反应的必要条件

项目成果

Takashi Harayama: "Internal Aryl-aryl Coupling Reaction Using a Novel and Highly Active Palladium Reagent Prepared from Pd(OAc)_2,DPPP,and Bu_3P" Chemical & Pharmceutical Bulletin. 45・10. 1723-1725 (1997)

Takashi Harayama：“使用由 Pd(OAc)_2、DPPP 和 Bu_3P 制备的新型高活性钯试剂进行内部芳基-芳基偶联反应”化学与制药公报 45・10 (1997)。

Takashi Harayama: "Concise Synthesis of Nitidine by Palladium-assisted Biaryl Coupling Reaction" Heterocycles. 49. 191-195 (1998)

Takashi Harayama：“通过钯辅助联芳基偶联反应简明合成两面针碱”杂环。

Takashi Harayama: "Internal Aryl-aryl Coupling Reaction Using a Novel and Highly Active Palladium Reagent Prepared from Pd(OAc)_2, DPPP, and Bu_3P" Chemical & Pharmaceutical Bulletin. 45・10. 1723-1725 (1997)

Takashi Harayama：“使用由 Pd(OAc)_2、DPPP 和 Bu_3P 制备的新型高活性钯试剂进行内部芳基-芳基偶联反应”化学与制药公报 45・10 (1997)。

Takashi Harayama: "A Concise Synthesis of Arnottin I via Internal Biaryl Coupling Reaction Using Palladium Reagent" Heterocycles. 46. 61-64 (1997)

Takashi Harayama：“使用钯试剂通过内部联芳基偶联反应简明合成 Arnottin I”杂环。

Takashi Harayama: "Synthesis of Benzo [C] phenanthridine Alkaloids, Chelerythrine and Nitidine Using a Novel palladium-Phosphine Combination System-Pd (OAc)_2, DPPP, and Bu_3P" Heterocycles. 48・10. 1989-1993 (1998)

Takashi Harayama：“使用新型钯-膦组合系统 - Pd (OAc)_2、DPPP 和 Bu_3P 合成苯并 [C] 菲啶生物碱、白屈菜红碱和两面针碱”杂环化合物 48・10。