An enone was synthesized from delta-D-gluconolactone in four steps, involving a one-pot TPAP oxidation-K2CO3-mediated intramolecular Horner-Wadsworth-Emmons (HWE) olefination as the key step. / In this thesis, a review regarding intramolecular direct aldol reaction from 1971 to 2008 is presented. The background information on pseudo-acarviosin, valiolamine and its containing compounds, gabosines and human glutathione transferase (hGST) is introduced. / Intramolecular direct aldol reaction was investigated for the construction of cyclohexanones and cycloheptanones from carbohydrates. Amine bases, amide bases and L-proline were employed to facilitate cyclization of 1,5- and 1,6-diketones successfully. These 1,5- and 1,6-diketones were prepared from carbohydrates by standard transformations. Different bases were employed to promote cyclization of 1,5-diketone derived from D-glucose to give cyclohexanones stereoselectively. / Intramolecular nitrile oxide-alkene cycloaddition (INOC) was studied with sugar derivatives having free hydroxyl groups. The INOC reaction, by incorporating chloramine-T and silica gel for the formation of nitrile oxide from oxime, proceeded smoothly with one, two, and four unmasked hydroxyl groups to give cyclopentanes and cyclohexanes. / The polyhydroxylated carbocycles constructed from sugars were successfully transformed into a variety of target molecules including pseudo-acarviosin, valiolamine and its containing compounds and gabosines. A series of 2-crotonyloxymethyl-(4 R,5R,6R)-4,5,6-trihydroxy-2-cyclohexenone (COTC) analogues as inhibitors of hGST were prepared in order to study the structure-activity relationships. / Cheng, Hau Man. / Adviser: Tony K. M. Shing. / Source: Dissertation Abstracts International, Volume: 70-06, Section: B, page: 3508. / Thesis (Ph.D.)--Chinese University of Hong Kong, 2008. / Includes bibliographical references (leaves 214-224). / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Electronic reproduction. [Ann Arbor, MI] : ProQuest Information and Learning, [200-] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Abstracts in English and Chinese. / School code: 1307.
| Identifer | oai:union.ndltd.org:cuhk.edu.hk/oai:cuhk-dr:cuhk_344274 |
| Date | January 2008 |
| Contributors | Cheng, Hau Man., Chinese University of Hong Kong Graduate School. Division of Chemistry. |
| Source Sets | The Chinese University of Hong Kong |
| Language | English, Chinese |
| Detected Language | English |
| Type | Text, theses |
| Format | electronic resource, microform, microfiche, 1 online resource (vii, 226 leaves : ill.) |
| 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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