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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

Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 1982. / MICROFICHE COPY AVAILABLE IN ARCHIVES AND SCIENCE / Vita. / Includes bibliographical references. / by Catherine Ann Seymour. / Ph.D.

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Thesis (M. Phil.)--University of Hong Kong, 1987.

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The synthesis of methyl 3,6-dimethylpyridine-2-carboxylate (192) by the Diels-Alder addition of 3-butene-2-one dimethylhydrazone (190) and methyl-2-butynoate (16) is described. The structure of 192 was confirmed by the synthesis of methyl 2,6-dimethylpyridine-3-carboxylate (195), the opposite regioisomer.The synthesis of methyl 3,5-dimethylpyridine-2-carboxylate (199) from [4+2] cycloaddition of 2-methyl-2-propenal dimethylhydrazone (171) and 16 is described. In addition to producing a small amount of 199 directly, the reaction produced an intermediate of possible structure 198 which yielded 199 on catalytic dehydrogenation.On prolonged heating, 2-acetyl-5-methylpyridine (200) was produced by the reaction of diene 171 with methyl vinyl ketone (176).The preparation of 2-cyan-5-methylpyridine (201) from the tetrahydropyridine derivative 175 via catalytic dehydrogenation is described.The synthesis of 5,7-dioxo-3-methyl-6-phenyl-1,1.,5,6,7-pentahydropyrroloC3,1.-b] pyridine (202) through the Diels-Alder addition of diene 171 and N-phenylmaleimide (149) is described. Also reported is the preparation of 5,7-dioxo-3-methyl-6-phenyl-3,5,6-trihydropyrrolo [3,1+-b]pyridine (203) via dehydrogenation of 202. / Department of Chemistry

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No description available.