published_or_final_version / Chemistry / Master / Master of Philosophy

published_or_final_version / abstract / Chemistry / Doctoral / Doctor of Philosophy

published_or_final_version / abstract / Chemistry / Doctoral / Doctor of Philosophy

A thesis presented in the University of the Witwatersrand for the degree of Doctor of Philosophy / AC 2018

by Fung Wing-chuen. / Thesis (M.Phil.)--Chinese University of Hong Kong, 1994. / Includes bibliographical references (leaves 57-59). / Abstract --- p.i / Acknowledgments --- p.ii / Biography --- p.iii / Abbreviation --- p.v-vi / Chapter 1. --- Introduction / Chapter 1.1 --- Natural O-heterocycles --- p.1 / Chapter 1.2 --- Methods for the construction of O-heterocycles --- p.5 / Chapter 1.3 --- Intramolecular nitrone cycloaddition in the construction of O-heterocycles --- p.9 / Chapter 2. --- Results and discussion / Chapter 2.1 --- Introduction --- p.12 / Chapter 2.2 --- Synthesis of 68，77，84 Via INC --- p.13 / Chapter 2.3 --- Acyclic INC of nitrones --- p.16 / Chapter 2.4 --- "Studies on 7-, 8-membered rings formation" --- p.24 / Chapter 3. --- Conclusions --- p.29 / Chapter 4. --- Experimental --- p.34 / Chapter 5. --- References --- p.57 / Chapter 6. --- List of spectra --- p.60 / Chapter 7. --- Appendices --- p.72

by Yong-li Zhong. / Thesis (Ph.D.)--Chinese University of Hong Kong, 1998. / Includes bibliographical references (p. 234-246). / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Mode of access: World Wide Web.

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.

Wong Wai Fun. / "June 2006." / Thesis (Ph.D.)--Chinese University of Hong Kong, 2006. / Includes bibliographical references (p. 226-230). / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Abstracts in English and Chinese.

by Yip Ting. / Thesis submitted in 1997. / Thesis (M.Phil.)--Chinese University of Hong Kong, 1998. / Includes bibliographical references (leaves 55-59). / Abstract also in Chinese. / Acknowledgment --- p.i / Table of Contents --- p.ii / Abstract --- p.iii / Abbreviation --- p.iv / Chapter Part 1 --- Introduction --- p.1 / Chapter 1.1 --- General Background --- p.1 / Chapter 1.2 --- Review on the Published Syntheses of Zoapatanol --- p.2 / Chapter Part 2 --- Results and Discussion --- p.12 / Chapter 2.1 --- Synthetic Strategy --- p.12 / Chapter 2.1.1 --- Synthesis of Tertiary Alcohol46 --- p.14 / Chapter 2.1.2 --- Synthesis of Vinyl Bromide 55-Z --- p.15 / Chapter 2.1.3 --- Synthetic studies on39 --- p.18 / Chapter 2.1.4 --- Synthetic studies on40 --- p.19 / Chapter 2.2 --- Synthetic Strategy --- p.23 / Chapter 2.2.1 --- Synthesis of 79 - route1 --- p.24 / Chapter 2.2.2 --- Synthesis of 79 - route2 --- p.26 / Chapter 2.2.3 --- Synthesis of 79 - route3 --- p.28 / Chapter 2.2.4 --- Synthetic studies on free radical cyclization of79 --- p.30 / Chapter 2.2.5 --- Synthesis of83 --- p.31 / Chapter 2.2.6 --- Synthetic studies on carbanion cyclization of83 --- p.31 / Chapter Part 3 --- Conclusion --- p.33 / Chapter Part 4 --- Experimental --- p.34 / Chapter Part 5 --- References --- p.55

Kwok, Wun Sang. / Thesis (M.Phil.)--Chinese University of Hong Kong, 2007. / Includes bibliographical references (leaves 147-152). / Abstracts in English and Chinese. / Acknowledgment --- p.i / Table of Contents --- p.ii / Abstract --- p.iii / Abstract (Chinese Version) --- p.iv / Abbreviation --- p.v / Chapter 1. --- Introduction --- p.1 / Chapter 1.1 --- General Background --- p.1 / Chapter 1.1.1 --- "1,3-Dipolar Cycloaddition" --- p.1 / Chapter 1.1.2 --- Structure of Preparation of Nitrile Oxide --- p.3 / Chapter 1.2 --- Intramolecular Nitrile Oxide Alkene Cyclization (INOC) --- p.7 / Chapter 1.2.1 --- INOC in Organic Synthesis --- p.7 / Chapter 1.2.2 --- Formation of Oximolactone as Unwanted Reaction in INOC --- p.10 / Chapter 1.2.3 --- Nitrile Oxide Alkene Cyclization with Free Hydroxyl Group --- p.11 / Chapter 1.3 --- Natural Occurring Gabosine --- p.14 / Chapter 1.3.1 --- "Structure, Biological Effect and Syntheses of Gabosines" --- p.14 / Chapter 1.3.2 --- Synthesis of Gabosine O and its 4-epimer --- p.17 / Chapter 1.4 --- Protected 6-dehydroxy-Pseudo-a-D-Talose --- p.21 / Chapter 1.4.1 --- Structures and Biological Effects of Valienamine and its Derivatives --- p.21 / Chapter 1.4.2 --- Structural and Biological Studies of Valienamine by Our Group --- p.23 / Chapter 2. --- Results and Discussion --- p.28 / Chapter 2.1 --- Studies on INOC of Sugar Derivatives with Free Hydroxyl Group(s) --- p.28 / Chapter 2.2 --- Enantiospecific Synthesis of 4-epi-Gabosine O --- p.47 / Chapter 2.3 --- Enantiospecific Synthesis of Gabosine O --- p.84 / Chapter 2.4 --- Synthesis of 6-Deoxy-Pseudo-a-D-Talose --- p.87 / Chapter 3. --- Conclusion --- p.95 / Chapter 4. --- Experimental --- p.100 / References --- p.147 / Appendix NMR spectra --- p.153