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Synthesis of 3,4-disubstituted furans and 3-substituted furans using 3,4-bis(tri-n-butylstannyl)furan and 3-(tri-n-butylstainnyl)furan as building blocks.

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

Identiferoai:union.ndltd.org:cuhk.edu.hk/oai:cuhk-dr:cuhk_319116
Date January 1993
ContributorsYang, Yün., Chinese University of Hong Kong Graduate School. Division of Chemistry.
PublisherChinese University of Hong Kong
Source SetsThe Chinese University of Hong Kong
LanguageEnglish
Detected LanguageEnglish
TypeText, bibliography
Formatprint, vi, 120, 45 leaves : ill. ; 30 cm.
RightsUse 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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