Selectivity in the Synthesis of Cyclic Sulfonamides : Application in the Synthesis of Natural Products / by Kimberly Geoghegan

By:

Geoghegan, Kimberly [aut]

Resource type: Ressourcentyp: Buch (Online)Book (Online)Language: English Series: Springer Theses, Recognizing Outstanding Ph.D. Research | SpringerLink BücherPublisher: Cham ; s.l. : Springer International Publishing, 2014Description: Online-Ressource (XIII, 151 p. 257 illus., 24 illus. in color, online resource)ISBN:

9783319103389

Subject(s):

Additional physical formats: 9783319103372 | Erscheint auch als: 978-331-91033-7-2 Druck-AusgabeDDC classification:

LOC classification:

QD415-436

DOI: DOI: 10.1007/978-3-319-10338-9Online resources:

Contents:

Supervisor's Foreword; Contents; Abbreviations; 1 Introduction; 1.1emspAlkaloids; 1.2emspSceletium Alkaloids; 1.3emspThe First Total Synthesis of Mesembrine; 1.4emspAnnulation of Endocyclic Enamine; 1.5emspFirst Asymmetric Synthesis of Mesembrine; 1.6emspPhotocycloaddition of Vinylogous Amides; 1.7emspZirconium-Promoted Cyclisation; 1.8emspC&hx2013; H Insertion Construction of Quaternary Carbon Centres; 1.9emspStereocontrolled ZnBr2-Catalysed Rearrangement of 2,3-Aziridino Alcohols; 1.10emspOxy-Cope/Alkylation Sequence for the Formation of Quaternary Carbon Centres

1.11emspPalladium-Catalysed Sequential Arylation and Alkylation1.12emspAromatic Ring Umpolung; 1.13emspAsymmetric Hydrogenation Approach; 1.14emspAim; References; 2 Regioselectivity in the Heck (Mizoroki-Heck) Reaction; 2.1emspGeneral Introduction; 2.2emspIntermolecular Heck Reaction; 2.3emspIntramolecular Heck Reaction; 2.4emspRegioselectivity in the Intramolecular Heck Reaction of Sulfonamides; References; 3 Wagner-Meerwein Rearrangement of Cyclic Sulfonamides; 3.1emspIntroduction; 3.2emspBromonium Ion Mediated Migration of Bicyclic Compounds

3.3emspBromonium Ion Migration of Tricyclic CompoundsReferences; 4 An Investigation into the One-Pot Heck Olefination-Hydrogenation Reaction; 4.1emspIntroduction; 4.2emspIntramolecular Heck-Hydrogenation Sequence; 4.3emspIntermolecular Heck-Hydrogenation Sequence with Bromobenzene; 4.4emspIntermolecular Heck-Hydrogenation Sequence with Methyl Acrylate; References; 5 Double Reduction of Cyclic Aromatic Sulfonamides; 5.1emspIntroduction; 5.2emspTotal Synthesis of (±)-Mesembrane; 5.3emspTotal Synthesis of (−)-Mesembrine; References; 6 Experimental; 6.1emspGeneral Directions; 6.2emspExperimental

ReferencesAppendix

Summary: In the area of organic chemistry one major challenge we are currently faced with is how to assemble potentially useful molecules in new ways that generate molecular complexity and in sequences that are as efficient as possible. Our efforts in this regard, specifically for the preparation of amino containing compounds incorporating an aromatic ring, are described in this doctoral thesis. We discovered an interesting regioselectivity in an intramolecular Heck reaction, which we studied for a series of substrates that are unbiased in terms of the size of the newly formed ring, where very high levels of selectivity in relation to the new carbon-carbon bond are typically observed. DFT calculations were performed to attempt to shed light on the reaction sequence. This regioselective Heck reaction, combined with the reductive removal of the temporary amino-protecting group, allowed us to synthesize the Sceletium alkaloids: mesembrane, mesembranol and mesembrinePPN: PPN: 1659083656Package identifier: Produktsigel: ZDB-2-CMS

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