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Table Of Contents

1.4. The objectives of organic synthesis
1.5. New times, new targets?
1.8. Molecular complexity and synthetic analysis
2.3. Classification of functional groups according to D.A. Evans
2.4. Consonant and dissonant bifunctional relationships
3. METHODOLOGIES. SYNTHESIS TREE
The synthesis tree
3.2. Biogenetic considerations. Biomimetic synthesis
3.3. Mass Spectra and Retro-Mass Spectral Synthesis
HETEROLYTIC DISCONNECTIONS: HEURISTIC PRINCIPLES
4.1. Symmetry
4.2. Functional groups
4.3. The carbon skeleton: chains, rings and appendages
5. SYNTHESIS OF DISSONANT SYSTEMS
5.1. Illogical disconnections: reactivity inversion
5.2. Plausible disconnections: dissonant three-membered rings
5.3. Si gmatropic rearrangements
5.4. Reconnection of bifunctional dissonant systems to rings
5.5.1. Pinacol-type condensations
5.5.2. Acyloin condensation
5.5.3. Oxidative coupling of enolates
5.5.4. Electrochemical couplings
5.5.5. Double deprotonation ("LUMO-filled" msystems)
REFERENCES
6. MONOCYCLIC AND POLYCYCLIC SYSTEMS
6.1. Retro-annulations
6.1.1. Heterolytic disconnections
6.1.2. "Transition metal-mediated" cycloeliminations
6.3. Heterocyclic compounds
7.2.1. Strategic bonds: Corey's rules
SYSTEMS
8.1. Introduction
8.2. Specificity, selectivity, order and negative entropy
8.3. Diastereoselectivity in monocyclic and polycyclic systems
8.3.1. Conformational stereochemical control
8.3.2. Configurational stereochemical control
8.3.3. Proximity effects
9. ACYCLIC STEREOSELECTION
9.1.1. The sulphur atom as bridging element
9.1.2. Woodward's synthesis of erythronolide A
9.2.2. Boron enolates as "modulators" in acyclic diastereoselection
9.3. Enantioselective control
9.3.1. Strategies
9.3.4. "Double asymmetric induction"
10.1. Epoxidation of olefinic double bonds
10.1.1. Sharpless asymmetric epoxidation of allylic alcohols
10.1.2. Asymmetric epoxidation by alcohol substitution pattern
10.1.3. Kinetic resolution of allylic alcohols
10.1.4. Nucleophilic ring opening of epoxy alcohols
FUTURE. ENZYMES AND ANTIBODIES
11.1. Enantioselectivity in industry. An overview
11.2. Asymmetric synthesis
11.3. Enzymatic methods
11.3.1. Enzymes
11.3.3. Reversible inhibitors: transition state analogs 34
11.4.1. Chemistry and immunology. Antibodies
11.4.2. Polyclonal antibodies
11.4.3. Monoclonal antibodies. Hybridoma technology
11.4.4. Catalytic antibodies (antibodies as enzymes)
11.4.5. Protocol for immunological activation of small haptens
11.4.6. Transition state analogs and entropy traps
11.4.7. Carbonate, ester and amide hydrolysis
11.4.8. Cyclisation reactions
11.4.9. CIaisen rearrangement: chorismic acid to prephenic acid
11.4.10. Diels-Alder reactions
12. CONTROL ELEMENTS. SUMMARY
12.1. Control elements
12.1.3. Stereoselective control elements
12.2. Logic-centred synthetic analysis methodology: Summary
12.3. General strategies
13. SELECTED ORGANIC SYNTHESES
13.1. TWISTANE
13.2. LUCIDULINE
13.2.1. The total synthesis of racemic luciduline
13.3. CARYOPHYLLENES
13.4. SWAINSONINE: Sharpless synthesis
13.5.1. Stereocontrolled synthesis of 1, 3, 5...(2n +1) polyols
13.6. TAXOL
13.6.1. Structural features of taxol
13.6.2. Nicolaou's total synthesis of taxol
13.6.3. Holton's total synthesis of taxol
PART B. COMPUTER-ASSISTED ORGANIC SYNTHESIS
INTELLIGENCE. THE "EXPLORATION TREE"
14.1. Software available for computer-assisted organic synthesis
14.2.1. CHA OS
14.2.2. Modules of the CHAOS program
14.2.3. The "heuristic principles" as a guide to "disconnections"
14.2.6. Some general remarks on disconnection groups
14.2.7. About some special algorithms implemented in CHAOS
14.2.8. Limitations of CHAOS
UGrS THEORY OF CHEMICAL CONSTITUTION: EROS AND IGOR
1.1. Disk Contents and Hardware requirements
1.2. Use of the Macintosh | computer and the Windows | system
1.3. Installation of the programs
1.4. Learning the programs
1.5. How this manual is organised
2. RUNNING THE CHAOS PROGRAM
2.1. The Molecules editor
2.2. The Processing screen
2.3. Other available options
2.4. Limitations of the CHAOS program
3. R UNNING THE CHAOSBASE PROGRAM
3.1. Introduction
3.2. Functioning of the CHAOSBASE program
CHAOS: TABLES OF DISCONNECTION GROUPS
GROUP 7- HETEROCYCLIC DISCONNECTIONS
SUGGESTED EXERCISES TO BE SOLVED BY CHAOS
SUBJECT INDEX
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056 Organic Chemistry in Action

056 Organic Chemistry in Action

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Published by: biofaares on Mar 30, 2011
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