Umfang:
Online-Ressource (XIX, 184 p. 256 illus., 12 illus. in color, online resource)
ISBN:
9783319044620
Serie:
Springer Theses, Recognizing Outstanding Ph.D. Research
Inhalt:
In his thesis, Kiyoun Lee describes his studies into tandem and organocatalytic oxa-conjugate addition reactions for the synthesis of complex tetrahydropyrans (THP). Readers gain insight into the new methods Lee employs for the synthesis of biologically interesting natural products including (+)-leucascandrolide A, (+)-dactylolide, and (±)-diospongin A. The reactions Lee investigates are applicable to a broad range of substrates and proceed with excellent stereoselectivity. Moreover, the methodologies allow the synthesis of a wide range of THP-containing compounds. The development of reactions, such as those discussed by Lee, has the potential to impact natural product synthesis, pharmaceutical development and chemical biology.
Anmerkung:
Description based upon print version of record
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Supervisor's Foreword; Abstract; Acknowledgments; Contents; Abbreviations; 1 Introduction; 1.1…Significance; 1.2…General Approaches to the Synthesis of Substituted Tetrahydropyrans; 1.2.1 Prins Cyclization Reaction; 1.2.2 Petasis--Ferrier Rearrangement; 1.2.3 Hetero-Diels--Alder Reaction (HDA); 1.2.4 Radical Cyclization; 1.2.5 Transition Metal-Mediated Cyclization; 1.2.6 Epoxide-Mediated Cyclization; 1.2.7 Summary; References; 2 Stereoselective Synthesis of Tetrahydropyrans via Tandem and Organocatalytic Oxa-Conjugate Addition Reactions; 2.1…Introduction; 2.2…Preliminary Study
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2.2.1 Design of the Tandem Oxidation/Oxa-Conjugate Addition2.2.2 gem-Disubstituent Effect on Reaction Rate and Stereoselectivity; 2.3…Result and Discussion; 2.3.1 Tandem and Organocatalytic Oxa-Conjugate Addition; 2.3.1.1 Conformational Analysis of the Oxa-Conjugate Addition Reaction; 2.3.1.2 Synthesis of 2,3-trans-2,6-trans-Tetrahydropyrans; 2.3.1.3 Synthesis of 2,3-trans-2,6-cis- and 2,3-cis-2,6-cis-Tetrahydropyrans; 2.3.1.4 Synthesis of the Tetrahydropyran Cores of ent-(+)-Sorangicin A; 2.3.1.5 Conclusion; 2.3.1.6 Experimental Section; 2.3.2 Formal Synthesis of (+)-Leucascandrolide A
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2.3.2.1 Background2.3.2.2 Previous Syntheses of Leucascandrolide A; 2.3.2.3 Retrosynthetic Analysis of (+)-Leucascandrolide A; 2.3.2.4 Synthesis of 2,3-trans-2,6-trans-Tetrahydropyran via Organocatalytic Oxa-Conjugate Addition Reaction; 2.3.2.5 Synthesis of Bis-Tetrahydropyran; 2.3.2.6 Completion of Formal Synthesis of (+)-Leucascandrolide A; 2.3.2.7 Conclusion; 2.3.2.8 Experimental Section; 2.3.3 Total synthesis of (+)-Dactylolide; 2.3.3.1 Background; 2.3.3.2 Previous Syntheses of Dactylolide; 2.3.3.3 Retrosynthetic Analysis of (+)-Dactylolide
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2.3.3.4 Synthesis of 2,6-cis-Tetrahydropyran via Intramolecular Organocatalytic 1,6-Oxa-Conjugate Addition Reaction2.3.3.5 Synthesis of omega -Hydroxy Aldehyde; 2.3.3.6 NHC-Catalyzed Oxidative Macrolactonization; 2.3.3.7 Completion of Total Synthesis of (+)-Dactylolide; 2.3.3.8 Conclusion; 2.3.3.9 Experimental Section; References; 3 Synthesis of 4-Hydroxy-2, 6-cis-Tetrahydropyrans via Tandem Cross-Metathesis/Thermal SN2vprime Reaction; 3.1…Introduction; 3.2…Preliminary Study; 3.3…Results and Discussion; 3.3.1 Tandem Cross-Metathesis/Thermal SN2vprime Reaction
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3.3.2 Synthesis of (±)-Diospongin A3.4…Conclusion; 3.5…Experimental Section; References; Biography
Weitere Ausg.:
ISBN 9783319044613
Weitere Ausg.:
Erscheint auch als Druck-Ausgabe ISBN 978-331-90446-1-3
Sprache:
Englisch
DOI:
10.1007/978-3-319-04462-0
URL:
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