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首頁(yè)> 外文學(xué)位 >Part I. Asymmetric organocatalysis: (1) Direct enantioselective organocatalytic hydroxymethylation of aldehydes catalyzed by alpha,alpha-diphenylprolinol trimethylsilyl ether: Application in the formal synthesis of (-)-Rasfonin; (2) Synthesis of a novel bicyclic secondary amine organocatalyst: Application to the direct enantioselective organocatalytic hydroxymethylation of aldehydes. Part II. Asymmetric synthesis of bicyclic analogues of the anti-osteoporotic drug risedronate.
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Part I. Asymmetric organocatalysis: (1) Direct enantioselective organocatalytic hydroxymethylation of aldehydes catalyzed by alpha,alpha-diphenylprolinol trimethylsilyl ether: Application in the formal synthesis of (-)-Rasfonin; (2) Synthesis of a novel bicyclic secondary amine organocatalyst: Application to the direct enantioselective organocatalytic hydroxymethylation of aldehydes. Part II. Asymmetric synthesis of bicyclic analogues of the anti-osteoporotic drug risedronate.

機(jī)譯：第一部分，不對(duì)稱(chēng)有機(jī)催化：（1）α，α-二苯基脯氨醇三甲基甲硅烷基醚催化的醛的直接對(duì)映選擇性有機(jī)催化羥甲基化：在（-）-Rasfonin的正式合成中的應(yīng)用； （2）新型雙環(huán)仲胺有機(jī)催化劑的合成：應(yīng)用于醛的直接對(duì)映選擇性有機(jī)催化羥甲基化。第二部分抗骨質(zhì)疏松藥物Risedronate的雙環(huán)類(lèi)似物的不對(duì)稱(chēng)合成。

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Part I. Asymmetric Organocatalysis: (1) Direct Enantioselective Organocatalytic Hydroxymethylation of Aldehydes Catalyzed by alpha,alpha-Diphenylprolinol Trimethylsilyl Ether: Application in the Formal Synthesis of (-)-Rasfonin; (2) Synthesis of a Novel Bicyclic Secondary Amine Organocatalyst: Application to the Direct Enantioselective Organocatalytic Hydroxymethylation of Aldehydes. An efficient and synthetically useful enantioselective organocatalytic hydroxymethylation of aldehydes catalyzed by alpha,alpha-diphenylprolinol trimethylsilyl ether has been developed with excellent enantioselectivity and a broad substrate scope. The hydroxymethylation methodology was applied to a short formal synthesis of (-)-Rasfonin; an apoptosis inducer in ras dependent cells. Several novel camphor-based secondary amine catalysts were synthesized via addition of a Grignard reagent to an activated imine which was efficiently synthesized by treatment of a lactam with Cp 2Zr(H)Cl. Moderate to good enantioselectivity (up to 80%) in the organocatalytic enantioselective hydroxymethylation reaction were achieved with these catalyst systems.;Part II. Asymmetric Synthesis of Bicyclic Analogues of the Antiosteoporotic Drug Risedronate. An enantioselective synthesis of the potentially potent anti-osteoporotic drug 6,7-dihydro-5H-cyclopenta[ c]pyridine-7-yl)methyldiphosphonic acid hydrochloride salt and 6,7-dihydro-5 H-cyclopenta[c]pyridine-7-yl)-2-hyroxydiphosphonic acid hydrochloride salt were achieved. The molecules were both achieved by utilizing an enantioselective organocatalytic hydroxymethylation reaction and an intramolecular aza Diels-Alder reaction. The synthesis can be modified for the enantiomer of the bisphosphonic acid through use of the catalyst antipode. Short racemic syntheses of 2-(2,3-dihydro-1H-inden-1-yl)-bisphosphonic acid and 2-(2,3-dihydro-1H-inden-1-y1)-2-hydoxybisphosphonic acid were achieved for comparison of their activity to the nitrogen-containing analogues. The bisphosphonates synthesized will be used as molecular probes for nitrogen-containing bisphosphonate-mediated anti-osteoporosis studies.
機(jī)譯：第一部分：不對(duì)稱(chēng)有機(jī)催化：（1）由α，α-二苯基脯氨醇三甲基甲硅烷基醚催化的醛的直接對(duì)映選擇性有機(jī)催化羥甲基化：在（-）-Rasfonin的形式合成中的應(yīng)用； （2）新型雙環(huán)仲胺有機(jī)催化劑的合成：應(yīng)用于醛的直接對(duì)映選擇性有機(jī)催化羥甲基化。已經(jīng)開(kāi)發(fā)了具有優(yōu)異的對(duì)映選擇性和廣泛的底物范圍的由α，α-二苯基脯氨醇三甲基甲硅烷基醚催化的醛的有效和合成上有用的對(duì)映選擇性有機(jī)催化羥甲基化。將羥甲基化方法學(xué)應(yīng)用于（-）-Rasfonin的短式正式合成； ras依賴性細(xì)胞中的凋亡誘導(dǎo)劑。通過(guò)向活化的亞胺中添加格氏試劑，合成了幾種新型的基于樟腦的仲胺催化劑，該亞胺通過(guò)用Cp 2Zr（H）Cl處理內(nèi)酰胺而有效合成。用這些催化劑體系在有機(jī)催化的對(duì)映選擇性羥甲基化反應(yīng)中達(dá)到了中等至良好的對(duì)映選擇性（高達(dá)80％）?？构琴|(zhì)疏松藥物利塞膦酸雙環(huán)類(lèi)似物的不對(duì)稱(chēng)合成。對(duì)映選擇性合成潛在有效的抗骨質(zhì)疏松藥物6,7-二氫-5H-環(huán)戊[c]吡啶-7-基）甲基二膦酸鹽鹽酸鹽和6,7-二氫-5H-環(huán)戊[c]吡啶-7得到-（基）-2-羥基二膦酸酯鹽酸鹽。通過(guò)利用對(duì)映選擇性的有機(jī)催化羥甲基化反應(yīng)和分子內(nèi)的氮雜Diels-Alder反應(yīng)來(lái)獲得分子。通過(guò)使用催化劑對(duì)映體，可以對(duì)雙膦酸的對(duì)映異構(gòu)體進(jìn)行合成修飾。獲得了2-（2,3-二氫-1H-茚滿-1-基）-雙膦酸和2-（2,3-二氫-1H-茚滿-1-y1）-2-羥基雙膦酸的短消旋合成。它們的活性與含氮類(lèi)似物的比較。合成的雙膦酸酯將用作含氮雙膦酸酯介導(dǎo)的抗骨質(zhì)疏松研究的分子探針。

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  • 作者

    Miller, John Robert.;

  • 作者單位

    University of Rochester.;

  • 授予單位 University of Rochester.;
  • 學(xué)科 Health Sciences Pharmacology.;Chemistry Organic.
  • 學(xué)位 Ph.D.
  • 年度 2010
  • 頁(yè)碼 364 p.
  • 總頁(yè)數(shù) 364
  • 原文格式 PDF
  • 正文語(yǔ)種 eng
  • 中圖分類(lèi)
  • 關(guān)鍵詞

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