by Eric Kwok Wai Tam. / Thesis (Ph.D.)--Chinese University of Hong Kong, 1996. / Includes bibliographical references. / Table of Contents --- p.i / Acknowledgement --- p.iv / Abstract --- p.v / Abbreviation --- p.vii / Part A / Enantiospecific Syntheses of Cyclohexane Oxides from (-)-Quinic Acid / Chapter 1. --- Synthetic Application of (-)-Quinic Acid --- p.1 / Chapter 1.1 --- Introduction --- p.1 / Chapter 1.2 --- Syntheses of Cyclohexane Derivatives --- p.2 / Chapter 1.2.1 --- Syntheses of Shikimic Acid (2) and its Derivatives --- p.2 / Chapter 1.2.2 --- "Syntheses of D-myo-Inositol 1,4,5-Trisphosphate (52) & its analog" --- p.15 / Chapter 1.2.3 --- Syntheses of Mycosporins --- p.17 / Chapter 1.2.4 --- Synthesis of (+)-Palitantin (76) --- p.19 / Chapter 1.2.5 --- "Synthesis of 2-Crotonyloxy-(4R,5R,6R)-4,5,6-trihydroxy- cyclohex-2-enone (COTC) (82)" --- p.20 / Chapter 1.2.6 --- Syntheses of Cyclophellitol (83) and its Diastereomers --- p.21 / Chapter 1.2.7 --- Syntheses of Pseudo-sugars and its Derivatives --- p.24 / Chapter 1.2.8 --- Syntheses of Aminocyclitol Antibiotics --- p.34 / Chapter 1.2.9 --- Syntheses of A-ring Precursor of Daunomycin --- p.36 / Chapter 1.2.10 --- "Synthesis of 19-nor-lα,25-Dihydroxyvitamin D3" --- p.38 / Chapter 1.2.11 --- Synthesis of Isoquinuclidines --- p.41 / Chapter 1.2.12 --- Synthesis of Cyclohexenyl Iodide: Taxol CD-ring Precursor --- p.44 / Chapter 1.2.13 --- Synthesis of C-20 to C-34 Segment of FK-506 --- p.46 / Chapter 1.2.14 --- Synthesis of the Hexahydrobenzofuran Subunit of Avermectins --- p.49 / Chapter 1.2.15 --- Synthesis of Bicyclic Core of Enediyne --- p.50 / Chapter 1.2.16 --- Syntheses of Two Enantiopure Derivatives of 4-Hydroxy-2-cyclohexone --- p.53 / Chapter 1.3 --- Synthesis of Homochiral Linear Molecules --- p.57 / Chapter 1.3.1 --- Syntheses of (3S)-Mevalonolactone and its Derivatives --- p.57 / Chapter 1.3.2 --- Synthesis of the Subunit in Maytansinoids --- p.58 / Chapter 1.3.3 --- Synthesis of (+)-Negamycin --- p.59 / Chapter 1.3.4 --- Syntheses of Hepoxilins B3 and its Stereoisomers --- p.61 / Chapter 1.3.5 --- Synthesis of C-21 to C-25 Fragment of FK-506 --- p.62 / Chapter 1.4 --- Synthesis of Cyclopentane Derivatives --- p.63 / Chapter 1.4.1 --- Synthesis of 11 α-Hydroxy-13-oxaprostanoic Acid --- p.65 / Chapter 1.4.2 --- Synthesis of (-)-Pentenomycin I --- p.66 / Chapter 1.4.3 --- Syntheses of Carbovir and its Derivatives --- p.66 / Chapter 1.5 --- Synthesis of Cycloheptane Derivatives --- p.68 / Chapter 1.6 --- Conclusion --- p.70 / References --- p.71 / Chapter 2. --- Introduction of Cyclohexane Oxides --- p.81 / Chapter 2.1 --- General Background --- p.81 / Chapter 2.2 --- Previous Syntheses of Cyclohexane Oxides --- p.86 / Chapter 2.2.1 --- Racemic Syntheses of Crotepoxide --- p.86 / Chapter 2.2.2 --- Racemic Syntheses of Senepoxide --- p.89 / Chapter 2.2.3 --- A Racemic Synthesis of Pipoxide --- p.92 / Chapter 2.2.4 --- Syntheses of Enantiopure Cyclohexane Oxides --- p.93 / References --- p.96 / Chapter 3. --- Retrosynthetic Analysis and Strategy --- p.99 / Chapter 3.1 --- Antithetic Analysis of Cyclohexane Oxides --- p.99 / Chapter 3.2 --- Problems Encounter in the Conversion of Diene into Cyclohexane Oxides --- p.100 / Chapter 3.3 --- Photo-oxygenation Approach to Cyclohexane Oxides --- p.102 / Chapter 3.4 --- Reasons for Choosing the Silyl Ether as Blocking Group --- p.104 / Chapter 3.5 --- Strategy for Synthesis of Diene 373 from Quinic acid --- p.105 / References --- p.106 / Chapter 4. --- Results and discussion --- p.108 / Chapter 4.1 --- Synthesis of Silyl Benzoate381 --- p.108 / Chapter 4.2 --- Synthesis of Alkene373 --- p.111 / Chapter 4.3 --- Syntheses of (+)-Crotepoxide (289)，(+)-Bosenepoxide (290) and (-)-iso-Crotepoxide (304) --- p.115 / Chapter 4.4 --- "Syntheses of the (+)-β-Senepoxide (295)，(+)-Pipoxide Acetate (365), (-) Tintanoxide (294) and (-)-Senepoxide (291)" --- p.121 / References --- p.124 / Chapter 5. --- Conclusion --- p.126 / Chapter 6. --- Experimental Section --- p.128 / References --- p.142 / Part B / Ruthenium Catalyzed cis-Dihydroxylation of Alkene / Chapter 1. --- Introduction --- p.143 / Chapter 1.1 --- Background --- p.143 / Chapter 1.2 --- General cis-Dihydroxylation Methods --- p.144 / Chapter 1.2.1 --- Potassium Permanganate (KMnO4) --- p.144 / Chapter 1.2.2 --- Osmium Tetraoxide (OsO4) --- p.146 / Chapter 1.3 --- Ruthenium Tetraoxide Oxidations --- p.148 / Chapter 1.4 --- Previous Reports of Using Ruthenium Tetraoxide (RuO4) Mediated syn-Dihydroxylation of Olefins --- p.149 / Chapter 1.4.1 --- The Snatzke and Fehlhaber Work --- p.149 / Chapter 1.4.2 --- The Sharpless and Akashi Work --- p.150 / Chapter 1.4.3 --- The Sica and Co-workers Work --- p.150 / References --- p.152 / Chapter 2. --- Ruthenium-Catalyzed cis-Dihydroxylation of Alkenes --- p.155 / Chapter 2.1 --- """Flash"" Dihydroxylation" --- p.155 / Chapter 2.2 --- "Stereochemical Outcome of ""Flash"" Dihydroxylation" --- p.155 / References --- p.157 / Chapter 3. --- Results and Discussion --- p.158 / Chapter 3.1 --- "Scope and Limitations of ""Flash"" Dihydroxylation" --- p.158 / Chapter 3.2 --- "Study of the Diastereoselectivity of ""Flash"" Dihydroxylation" --- p.168 / Chapter 3.3 --- "Study of Co-oxidants for ""Flash"" Dihydroxylation" --- p.170 / Chapter 3.4 --- "Solvent Effect for ""Flash"" Dihydroxylation" --- p.171 / Chapter 3.5 --- "Synthetic Application of ""Flash"" Dihydroxylation" --- p.173 / References --- p.175 / Chapter 4. --- Conclusion --- p.176 / Chapter 5. --- Experimental Section --- p.177 / References --- p.185 / Appendix --- p.186
| Identifer | oai:union.ndltd.org:cuhk.edu.hk/oai:cuhk-dr:cuhk_321664 |
| Date | January 1996 |
| Contributors | Tam, Eric Kwok Wai., Chinese University of Hong Kong Graduate School. Division of Chemistry. |
| Publisher | Chinese University of Hong Kong |
| Source Sets | The Chinese University of Hong Kong |
| Language | English |
| Detected Language | English |
| Type | Text, bibliography |
| Format | print, viii, 186 leaves : ill. ; 30 cm. |
| 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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