Product Description
Gain an understanding of the latest advances in spectroscopy with the text that has set the unrivaled standard for more than 30 years: Pavia/Lampman/Kriz/Vyvyan's INTRODUCTION TO SPECTROSCOPY, 4e. This comprehensive resource provides an unmatched systematic introduction to spectra and basic theoretical concepts in spectroscopic methods that create a practical learning resource whether you're an introductory student or someone who needs a reliable reference text on spectroscopy. This well-rounded introduction features updated spectra; a modernized presentation of one-dimensional nuclear magnetic resonance (NMR) spectroscopy; the introduction of biological molecules in mass spectrometry; and inclusion of modern techniques alongside DEPT, COSY, and HECTOR. Count on this book's exceptional presentation to provide the comprehensive coverage you need to understand today's spectroscopic techniques.
Product Details
* Paperback: 656 pages
* Publisher: Brooks Cole; 4 edition (March 12, 2008)
* Language: English
* ISBN-10: 0495114782
* ISBN-13: 978-0495114789
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Classics in Stereoselective Synthesis
Erick M. Carreira, Lisbet Kvaerno
ISBN: 978-3-527-32452-1
Hardcover
651 pages
February 2009
This book provides a noteworthy compilation of the groundbreaking methods of stereoselective synthesis, belonging to the repertoire of every modern practitioner of synthetic organic chemistry. The general principles underlying these processes are highlighted as they form the basis for the rapid and continuing developments in the field. The work also features illustrative examples of drug and natural product syntheses, resulting in a rich source of stimulating ideas for the efficient use of asymmetric reactions in the construction of stereochemically complex structures.
MACROCYCLIC STEREOCONTROL
Introduction
Background
Conformational Control in Medium-Sized Rings
Asymmetric Synthesis with Medium-Sized Rings
Case Studies in Natural Products Total Synthesis
Macrocyclic Stereocontrol in Cyclic Peptides
Appendix: Macrocycle Formation
CARBONYL ADITION REACTIONS
Introduction
Non-Chelated 1,2-Asymmetric Induction and the Operation of Steric and Electronic Effects
1,2-Asymmetric Induction Predicated on Chelation Control
1,3-Asymmetric Induction from CBeta Stereogenic Centers
Asymmetric Induction by Remote Stereocenters (Beyond 1,3-Induction)
Catalytic Enantioselective Carbonyl Additions of Arganozinc Species
Enantioselective Ketone Reduction
Enzymatic Reduction of Ketones
Enantioselective Formation of Cyanohydrins
Enantioselective Alkyne Additions
Asymmetric Carbonyl-Ene Reactions
ALPHA-FUNCTIONALIZATIONS OF ENOLATES
Introduction
Diastereoselective Alpha-Alkylations of Chiral Enolates
Heteroatom-Substituted Enolates
Asymmetric Enolate Alkylations Using Chiral Auxiliaries
Enantioselective Enolate Alkylations
Alpha-Hydroxylations of Enolates
Alpha-Halogenations of Enolates
ALDOL REACTIONS
Introduction
Chiral Enolates Through the Use of Chiral Auxiliaries or Chiral Controller Groups
Substrate Control with Chiral Carbonyl Compounds
Catalytic Enantioselective Aldol Reactions
ALLYLATIONS OF C=O BONDS
Introduction
Reactivity of Allylmetal Reagents
Boronate Additions
Enantioselective Additions of Optically Active Allylic Boron Reagents
Diastereoselecive Allylations with Chiral Boron Reagents
Mechanistic Aspects ? Lewis Acid-Promoted Addition of Allylsilanes and Allylstannanes to Aldehydes
Chelation Control in the Allylation of Alpha- and Beta-Alkoxy Aldehydes
Allylchromium Reagents
Diastereoselective Allylations with Chiral Silanes and Stannanes
Catalytic Asymmetric Allylations
CHIRAL ACETALS
Introduction
Diastereoselective Reactions of Chiral Acetals
Glycosylations
Spiroketals in Natural Product Synthesis
ALKENE HYDROBORATION
Introduction
Hydroborations with Acyclic Stereocontrol
Metal-Catalyzed Hydroborations
Asymmetric Hydroborations with Chiral Boranes
Catalytic Asymmetric Hydroboration, Hydrosilylation, and Hydroalumination
REDUCTIONS OF OLEFINS
Introduction
Diastereoselective Olefin Reductions by Catalytic Hydrogenation
Alternative Methods for Diastereoselective Olefin Reductions
Catalytic Asymmetric Olefin Hydrogenations
OXIDATIONS OF OLEFINS
Introduction
Diastereoselective Epoxidations
Enantioselective Epoxidations
Asymmetric Ring-Opening of Epoxides
Synthesis of Aziridines
Iodolactonizations and Other Olefin Cyclizations Induced by Electrophiles
Diastereoselective Dihydroxylations of Olefins
Enantioselective Dihydroxylations of Olefins
Enantioselective Aminohydroxylation of Olefins
AMINO ACIDS
Introduction
Enantioselective Hydrogenations of Alpha, Beta-Didehydroamino Acids
Enolate Alkylations in the Presence of Chiral Auxiliaries
Alkylation of Glycine Anion Equivalents in the Presence of Chiral Phase-Transfer Catalysts
Enolate Aminations
Enzymatic Syntheses of Alpha-Amino Acids
Catalytic Asymmetric Strecker Reactions
ADDITIONS TO C=N BONDS
Introduction
Substrate-Controlled Diastereoselective Additions to C=N Bonds
Additions to Imine Derivatives Bearing N-Bound Auxiliaries
Formation of Beta-Lactams Through Staudinger Reactions
Intramolecular Diastereoselective Iminium Ion Cyclizations
Pictet-Spengler Reactions
Catalytic Asymmetric Reductions of Imines and Imine Derivatives
Catalytic Enantioselective Mannich and Mannich-Type Reactions
Enantioselective Additions of Carbon Nucleophiles to C=N Bonds
CONJUGATE ADDITIONS
Introduction
Diastereoselective Conjugate Additions
Diastereoselective Conjugate Additions with Use of Chiral Auxiliaries
Enantioselective Conjugate Additions of Enolates and other Stabilized Carbon Nucleophiles
Enantioselective Conjugate Additions of Organometallic Species
Enantioselective Conjugate Additions of Radicals
Enantioselective Conjugate Additions of Heteroatom Nucleophiles
Conjugate Reductions
Catalytic Enantioselective Stetter Reactions
CHIRAL CARBONIONS
Introduction
Organolithium Reagents by Transmetalation of Organostannanes
Carbanions by Reductive Methods
Chiral Carbanions by Deprotonation
Sulfoxide- and Phosphorus-Stabilized Carbanions
Metal-Mediated Enantioselective Olefin Functionalizations
METAL-CATALYZED ALLYLATIONS
Introduction
Diastereoselective Palladium-Catalyzed Allylation Reactions
Enantioselective Palladium-Catalyzed Allylation Reactions
Iridium-Catalyzed Enantioselective Allylation Reactions
Copper-Catalyzed SN2? Allylation Reactions
Enantioselective Allylation Reactions Catalyzed by Other Transition Metals
Asymmetric Ring-Opening Reactions of Unsaturated Heterocycles
CYCLOPROPANATIONS AND C-H INSERTION REACTIONS
Introduction
Diastereoselective Cyclopropanations with Carbenoids Generated from Diazoalkanes
Enantioselective Dyclopropanations with Carbenoids Generated from Diazoalkanes
Diastereoselective Simmons-Smith Cyclopropanations
Enantioselective Simmons-Smith Cyclopropanations
Alternative Classes Cyclopropanations
Diastereoselective C-H Bonds
SIGMATROPIC REARRANGEMENTS
Introduction
Claisen and Claisen-Type [3,3]-Sigmatropic Rearrangements
Cope and Cope-Type [3,3]-Sigmatropic Rearrangements
[2,3]-Sigmatropic Rearrangements
Ene Reactions
Nazarov Cyclizations
DIELS-ALDER AND HETERO-DIELS-ALDER REACTIONS
Introduction
Diastereoselective Intermolecular Diels-Alder Reactions
Diastereoselective Intramolecular Diels-Alder Reactions
Diastereoselective Diels-Alder Reactions Using Chiral Auxiliaries
Catalytic Enantioselective Diels-Alder Reactions
Diastereoselective Hetero-Diels-Alder Reactions
Enantioselective Hetero-Diels-Alder Reactions
[3+2]- AND [2+2]-CYCLOADDITION REACTIONS
Introduction
Substrate-Controlled Diastereoselective [1,3]-Dipolar Cycloadditions
Diastereoselective [1,3]-Dipolar Cycloadditions Using Chiral Auxiliaries
Catalytic Enantioselective [1,3]-Dipolar Cycloadditions
[3+2]-Cycloadditions with Trimethylenemethane Equivalents
Ketene Cycloadditions
Photochemical [2+2]-Cycloadditions
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Natural Product Chemistry at a Glance
Stephen P. Stanforth
ISBN: 978-1-4051-4562-6
Paperback
152 pages
August 2006, Wiley-Blackwell
Natural products have been a fertile area of chemical investigation for many years, driving the development of both analytical chemistry and of new synthetic reactions and methodologies. Many of the most important synthetic reactions in chemistry have been developed in the quest to characterise and synthesise these materials.
Natural Product Chemistry at a Glance provides a concise overview of the main principles and reactions of natural product chemistry, for students studying chemistry and related courses at undergraduate level. Based on the highly successful and student friendly “at a glance” approach, the material developed in this book has been chosen to reinforce the principles of elementary organic reactions and to highlight the similarity between many organic reactions and biological processes. It will also serve as an initial platform for more advanced excursions into the origin of natural products.
Students using Natural Product Chemistry at a Glance will find they have a resource with which they can quickly, economically and confidently acquire, regularly review and revise the basic facts that underpin the biosynthesis and chemistry of natural products.
Section 1: Introduction.
1.1 Primary and Secondary Metabolites.
1.2 Properties and Purpose of Secondary Metabolites.
Section 2: Acetyl Coenzyme A: A Key Biological Intermediate.
2.1 What is Acetyl Coenzyme A? 8.
2.2 Comparison of Organic and Acetyl Coenzyme A Reactions.
2.3 Malonyl Coenzyme A – A Partnership with Acetyl Coenzyme A.
2.4 How is Acetyl Coenzyme A Used in Biosynthesis?.
Section 3: Biosynthesis of Fatty Acids.
3.1 What are Fatty Acids?.
3.2 Occurrence and Function of Fatty Acids.
3.3 Biosynthesis of Saturated Straight-Chain Fatty Acids.
3.4 Biosynthesis of Saturated Branched Fatty Acids.
3.5 Mono-unsaturated Fatty Acids.
3.6 Poly-unsaturated Fatty Acid.
3.7 Oxygenated Fatty Acids.
3.8 β-Oxidation.
Section 4: Biosynthesis of Polyketides.
4.1 What are Polyketides?.
4.2 The Chemistry of 1,3-Dicarbonyls: Keto–Enol Tautomerism.
4.3 The Chemistry of 1,3-Dicarbonyls: Condensation Reactions.
4.4 Polyketide Cyclizations: Formation of Unsaturated Products.
4.5 Secondary Structural Modifications During Polyketide Cyclizations.
4.5.1 Alkylation.
4.5.2 Reduction.
4.5.3 Oxidation.
4.5.4 Decarboxylation.
4.5.5 Modifications to the Carbon Skeleton.
4.6 Alkaloids Derived from Polyketides.
4.7 The Use of Isotopes in the Elucidation of Biosynthetic Pathways.
Section 5: The Shikimic Acid Pathway.
5.1 Introduction.
5.2 Transamination.
5.3 Biosynthesis of Natural Products Derived from Cinnamic Acid.
5.4 Lignans.
5.5 Biosynthesis of Alkaloids.
5.5.1 Decarboxylation of Amino Acids and α-Keto Acids.
5.5.2 Pictet–Spengler Reaction.
5.5.3 Alkaloids Derived from Tryptophan.
5.5.4 Alkaloids Derived from Tyrosine.
Section 6: Terpenes.
6.1 What are Terpenes?.
6.2 Carbocations as Intermediates in Terpene Biosynthesis.
6.2.1 Hydride Shifts.
6.2.2 Alkyl Shifts.
6.2.3 Cyclizations.
6.3 Termination of Carbocations.
6.3.1 Loss of a Proton.
6.3.2 Addition of Water.
6.4 Terpene Biosynthesis.
6.4.1 Biosynthesis Initiated by Heterolysis of Pyrophosphates.
6.4.2 Biosynthesis from ‘Dimers’ of Pyrophosphates.
6.4.3 Biosynthesis Initiated by Protonation or Epoxidation of an Alkene.
Section 7: Natural Products Derived from Amino Acids.
7.1 Alkaloids.
7.2 Penicillins and Related Compounds 1.1 Primary and Secondary Metabolites.
7.3 Macrocyclic Peptides.
7.4 Porphyrins.
Section 8: Answers to Problems.
Section 9: Further Reading.
Index
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