本文綜述了氨催化的相關背景資料。此外，本文還描述了Jørgensen-Hayashi類型的二芳基脯氨醇硅醚催化劑。 / 通過烷基化反應，二羥基化反應和鄰二醇斷裂法反應，可以合成4-羥基化的1,7-二醛70 合成出的對稱的二醛是用來作為構建具有光學活性的羥基化環己烷101a, b的一個先導物，也是用來作為測試製備的糖原氨催化劑以溫和方式進行立體選擇性的一個平臺。 / 以D-阿拉伯糖為原料，按照本課題組的以前的合成策略，合成出了含有不同芳基和2,3-O保護基的七個新的手性羥基化的糖原氨催化劑（105, 131, 134, 146, 154, 157和160）。將這些催化劑應用在不對稱的分子內的羥醛縮合反應 (aldol reaction) 中，糖原氨催化劑134 (90%，93% ee) 和157 (94%，89% ee) 顯示出非常好的催化活性。 / 羥醛縮合反應的產物 (+)-101a和 (+)-101b的絶對構型是通過與已發表的文獻中的相似反應比較確定的。 / 以D-葡萄糖為原料，按照已報導過的的合成方法，合成出了一系列的手性羥基化的烯酮，這些手性羥基化的烯酮是抗癌試劑COTC的類似物。并測試了它們對正常細胞和癌細胞的細胞毒性，以及對所得的結果進行了討論。 / In this thesis, the background information on aminocatalysis is introduced. A review regarding Jørgensen-Hayashi type diarylprolinol silyl ether catalysts is presented. / 4-hydroxylated 1,7-dial 70 was synthesized via alkylation, dihydroxylation and glycol cleavage. The symmetrical dial was prepared as a precursor to construct optically active hydroxylated cyclohexane 101a,b and as a platform to test the stereoselectivities of the prepared amine catalysts in a facile manner. / Seven new chiral hydroxylated amine catalysts (105, 131, 134, 146, 154, 157 and 160) bearing different aromatic groups and 2,3-O protecting groups were synthesized from D-arabinose following established protocol. These catalysts were applied in asymmetric intramolecular aldol reaction and amine 134 (90%, 93% ee) and 157 (94%, 89% ee) displayed positive results. / The absolute configurations of aldol adduct (+)-101a and (+)-101b were sucessfully assigned by comparing to established literature work of a similar reaction. / A series of chiral hydroxylated enones were synthesized from D-glucose as anticancer COTC analogues following established procedures. Their cytotoxicities against normal and cancer cell lines were measured and discussed [with diagram]. / Detailed summary in vernacular field only. / Detailed summary in vernacular field only. / Detailed summary in vernacular field only. / Detailed summary in vernacular field only. / Detailed summary in vernacular field only. / Wu, Ho Tong. / Thesis (Ph.D.) Chinese University of Hong Kong, 2014. / Includes bibliographical references (leaves 129-135). / Abstracts also in Chinese.
| Identifer | oai:union.ndltd.org:cuhk.edu.hk/oai:cuhk-dr:cuhk_1077721 |
| Date | January 2014 |
| Contributors | Wu, Ho Tong (author.), Shing,, Kung Ming Tony (thesis advisor.), Chinese University of Hong Kong Graduate School. Division of Chemistry, (degree granting institution.) |
| Source Sets | The Chinese University of Hong Kong |
| Language | English, Chinese |
| Detected Language | English |
| Type | Text, bibliography, text |
| Format | electronic resource, electronic resource, remote, 1 online resource (vii, 351 leaves) : illustrations, computer, online resource |
| Rights | Use of this resource is governed by the terms and conditions of the Creative Commons “Attribution-NonCommercial-NoDerivatives 4.0 International” License (http://creativecommons.org/licenses/by-nc-nd/4.0/) |
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