by Yun Yang. / Thesis (Ph.D.)--Chinese University of Hong Kong, 1993. / Includes bibliographical references (leaves 111-118). / Acknowledgements --- p.i / Contents --- p.ii / Abstract --- p.v / List of Acronyms and Abbreviations --- p.vi / Chapter Chapter 1. --- Introduction / Chapter 1.1 --- Background --- p.1 / Chapter 1.2 --- Reactions of Furans / Chapter 1.2.1 --- Electrophilic Substitution --- p.3 / Chapter 1.2.2 --- Nucleophilic Substitution --- p.6 / Chapter 1.2.3 --- Addition Reaction --- p.9 / Chapter 1.2.4 --- Oxidation Reaction --- p.9 / Chapter 1.3 --- Review of Synthetic Methods for the Syntheses of Polysubstitued Furans --- p.11 / Chapter 1.3.1 --- "From 1,4-Dicarbonyl Compounds" --- p.11 / Chapter 1.3.2 --- From α-Haloketones --- p.12 / Chapter 1.3.3 --- From Hetero Diels-Alder and Retro-Diels-Alder Reactions --- p.15 / Chapter 1.3.4 --- From Alkynes / Chapter 1.3.4.1 --- Via Radical Cyclization --- p.16 / Chapter 1.3.4.2 --- Via Insertion of Isocyanides --- p.16 / Chapter 1.3.4.3 --- Via Addition of Carbenoids --- p.17 / Chapter 1.3.4.4 --- Via Pd-Catalyzed Addition and Cyclization Reactions --- p.19 / Chapter 1.3.5 --- FromAllenes / Chapter 1.3.5.1 --- Via Allenic Sulfonium Salts --- p.20 / Chapter 1.3.5.2 --- Via Rh or Ag Catalyzed Cyclization --- p.21 / Chapter 1.3.5.3 --- Via Acylium Ions Addition to Allenylsilanes --- p.21 / Chapter 1.3.5.4 --- Via Allenic Palladium Intermediates --- p.22 / Chapter 1.3.6 --- From Pyrylium Salts --- p.23 / Chapter 1.3.7 --- From Miscellaneous Sources --- p.24 / Chapter 1.4 --- "Review of Synthetic Methods for the Syntheses of 3,4-Disubstituted Furans" / Chapter 1.4.1 --- From Functionalization of Furan Ring --- p.25 / Chapter 1.4.1.1 --- "Modification of Diethyl Furan-3,4-dicarboxylate" --- p.25 / Chapter 1.4.1.2 --- Modification of 3-(Hydroxymethyl)furan --- p.27 / Chapter 1.4.1.3 --- "From Boroxines Derived from 3,4-Bis(trimethylsilyl)furan…" --- p.28 / Chapter 1.4.2 --- From Ylide --- p.29 / Chapter 1.4.3 --- "From 2-Butyne-l,4-diol" --- p.29 / Chapter 1.4.4 --- From Hetero Diels-Alder and Retro-Diels-Alder Reactions --- p.30 / Chapter 1.4.5 --- From Sulfolene --- p.31 / Chapter 1.5 --- Aim of the Present Work --- p.32 / Chapter Chapter 2. --- Results and Discussion / Chapter 2.1 --- "Synthesis of 3,4-Bis(tri-n-butylstannyl)furan (47) and 3-(Tri-n-butylstannyl)furan (48) from Bis(tri-n-butylstannyl)acetylene (49) and 4-Phenyloxazole (50)" --- p.34 / Chapter 2.2 --- Stille-type Palladium-catalyzed Cross-coupling Reactions with Various Organic Halides --- p.36 / Chapter 2.2.1 --- General Features of Stille's Reaction --- p.38 / Chapter 2.2.2 --- Solvents and Catalysts --- p.42 / Chapter 2.2.3 --- Isolation and Purification of Products --- p.45 / Chapter 2.2.4 --- Direct Coupling with Organic Halides --- p.45 / Chapter 2.2.4.1 --- Acid Chloride --- p.46 / Chapter 2.2.4.2 --- Aryl Halide --- p.51 / Chapter 2.2.4.3 --- Vinyl Halide --- p.53 / Chapter 2.2.4.4 --- Allylic Bromide --- p.53 / Chapter 2.2.4.5 --- Benzylic Halide --- p.54 / Chapter 2.2.5 --- Mechanistic Aspects / Chapter 2.2.5.1 --- Mechanism for the Stille's Reaction of Acid Chloride --- p.54 / Chapter 2.2.5.2 --- Mechanism for the Stille's Reaction of Aryl Halide --- p.56 / Chapter 2.2.6 --- Carbonylative Coupling --- p.59 / Chapter 2.2.7 --- Conclusion --- p.64 / Chapter 2.3 --- "Synthesis of Unsymmetrical 3,4-Disubstituted Furans via Lithiation of 3,4-Bis(tri-n-butylstannyl)furan (47)" / Chapter 2.3.1 --- Lithiation of Organotin Compounds: General Remarks --- p.65 / Chapter 2.3.2 --- "Lithiation of 3,4-Bis(tri-n-butylstannyl)furan (47) with n-BuLi" --- p.68 / Chapter 2.3.3 --- Trapping of 3-Lithium-4-(tri-n-butylstannyl)furan (63) with Electrophiles --- p.70 / Chapter 2.3.4 --- "Synthesis of Unsymmetrical 3,4-Disubstituted Furans from 3-Substituted-4-(tri-n-butylstannyl)furan (64) via Stille's Reactions" --- p.72 / Chapter 2.3.5 --- Conclusion --- p.75 / Chapter 2.4 --- Halogenation --- p.75 / Chapter Chapter 3. --- Application to Natural Product Synthesis / Chapter 3.1 --- "Synthesis of a Key Intermediate in the Total Synthesis of (20,S)-Camptothecin" --- p.79 / Chapter 3.2 --- Synthesis of an Analog of Lactaral --- p.80 / Experimental --- p.83 / References --- p.111 / Appendix --- p.119

Tsang Tsun-keung. / Thesis (M.Phil.)--Chinese University of Hong Kong, 2002. / Includes bibliographical references (leaves 73-78). / Abstracts in English and Chinese. / ACKNOWLEDGEMENTS --- p.i / CONTENTS --- p.ii / ABSTRACT --- p.iv / ABBREVIATIONS --- p.vii / Chapter CHAPTER 1 --- INTRODUCTION --- p.1 / Chapter 1.1 --- General Background --- p.1 / Chapter 1.1.1 --- Characteristics of sesquiterpenoid furanoeudesmanes --- p.1 / Chapter 1.1.2 --- Examples of trans-fused natural sesquiterpenoid furanoeudesmanes --- p.2 / Chapter 1.1.3 --- Examples of cis-fused natural sesquiterpenoid furanoeudesmanes --- p.3 / Chapter 1.1.3.1 --- Tubipofuran and 15-acetoxytubipofuran --- p.3 / Chapter 1.1.4 --- Examples of C9-C10 unsaturated natural sesquiterpenoid furanoeudesmanes --- p.6 / Chapter 1.2 --- Biosynthesis of Sesquiterpenoid Furanoeudesmanes --- p.7 / Chapter 1.3 --- Synthesis of Sesquiterpenoid Furanoeudesmanes --- p.9 / Chapter 1.3.1 --- Synthetic examples of trans-fused sesquiterpenoid furanoeudesmanes --- p.9 / Chapter 1.3.2 --- Synthetic examples of cis-fused sesquiterpenoid furanoeudesmanes --- p.10 / Chapter 1.3.2.1 --- "Linearly fused A/B trans- and A/B cis- furo[3,2-b] and furo[2,3-b] decalin derivatives" --- p.10 / Chapter 1.3.2.2 --- "(±)-14-Norfuranoeudesmane-4,5-dione" --- p.11 / Chapter 1.3.2.3 --- Tubipofuran and 15-acetoxytubipofuran --- p.12 / Chapter CHAPTER 2 --- RESULTS AND DISCUSSION --- p.18 / Chapter 2.1 --- Aim of Present Work --- p.18 / Chapter 2.2 --- C ring + A ring →AC ring → ABC ring Scheme A --- p.20 / Chapter 2.2.1 --- Preparation of C ring in Scheme A --- p.20 / Chapter 2.2.2 --- Preparation of A ring in Scheme A --- p.22 / Chapter 2.2.3 --- Formation of B ring in Scheme A --- p.26 / Chapter 2.3 --- C ring + A ring → AC ring → ABC ring Scheme B --- p.37 / Chapter 2.3.1 --- Preparation of C ring in Scheme B --- p.37 / Chapter 2.3.2 --- Preparation of A ring in Scheme B --- p.37 / Chapter 2.3.3 --- Formation of B ring in Scheme B --- p.38 / Chapter CHAPTER 3 --- CONCLUSION --- p.51 / Chapter CHAPTER 4 --- EXPERIMENTAL SECTION --- p.52 / REFERENCES --- p.73 / APPENDIX --- p.79 / Chapter I --- List of X-ray Crystallographic Data / Chapter II --- List ofNMR Spectra

by Yick Chung Yan. / Thesis (Ph.D.)--Chinese University of Hong Kong, 1999. / Includes bibliographical references (p. 109-116). / 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. / Abstracts in English and Chinese.

Typescript (photocopy) / v, 169 leaves : ill. ; 31 cm. / Title page, contents and abstract only. The complete thesis in print form is available from the University Library. / Thesis (Ph.D.) Dept. of Organic Chemistry, University of Adelaide, 1983

Two approaches to the tricyclic core of the furanoeremophilane sesquiterpenoids are described. The first approach entails a projected Diels-Alder/retro Diels-Alder reaction of an acetylenic oxazole 64. Construction of the pivotal aldehyde 67 commenced from ketone 68. The acetyenic moiety was then introduced via a Felkin-Ahn addition of lithiopropyne to aldehyde 67. The final conversion of the cyclohexanone 83 to the acetylenic triflate 65 was unsuccessful. Attempts at addition of lithiated 2-methyloxazole 88 to ketone 83 were also unsuccessful. The second approach exploited a new annulation strategy. The aldehyde 64 was advanced to the 2, 4, 6-triisopropylbenzene sulfonylhydrazone 102 and a Shapiro reaction of 102 then provided alcohol 96. The furyl stananne 114 was readily prepared via a six-step sequence from acetylacetaldehyde dimethyl acetal 106. Unification of allylic bromide 90 and stannane 114 was accomplished through a Stille cross coupling methodology and the resulting product 113 was advanced to the aldehyde 116. However, attempts at further oxidation of this aldehyde to the required acid 89 failed. An alternative furyl stananne 124 with a tert-butyldimethylsilyl substituent at the C2 position was prepared from 3-furoic acid. An analogous sequence to that used with 113 led to aldehyde 131 which was successfully cyclized with the aid of trimethylsilyl trifluromethanesulfonate and 2, 6-lutidine to the tricyclic structure 132. Oxidation of the epimeric mixture of alcohols, followed by stereoselective reduction and removal of the tert-butyldimethylsilyl group from alcohol 134, gave (±)-6β-hydroxyeuroposin (4). Oxidation experiments with 134 were shown to convert the furan in this structure to a butenolide characteristic of the eremophilenolides. / Graduation date: 2004

No description available.

Diss. (sammanfattning) Uppsala : Univ., 2004. / Härtill 4 uppsatser.

Thesis (Ph.D.) Dept. of Organic Chemistry, University of Adelaide, 1983. / Typescript (photocopy).

Thesis (Ph.D.)-- University of Wisconsin--Madison, 2008. / Includes bibliographical references. Also available on the Internet.

Thesis (M.S.)--Rochester Institute of Technology, 1991. / Includes bibliographical references.