Solid-phase organic synthesis / edited by Kevin Burgess.

Format:

Book

Contributor:

Burgess, Kevin L., 1968-

Language:

English

Subjects (All):

Organic compounds--Synthesis.

Organic compounds.

Solid-phase synthesis.

Physical Description:

xiv, 277 pages : illustrations ; 24 cm

Place of Publication:

New York : Wiley-Interscience, [2000]

Summary:

Combinatorial chemistry is a rapidly-growing field in organic and pharmaceutical synthesis. Articles on organic synthesis of solid support have grown exponentially over the last three years. This new work brings together the latest research in the field, highlighting and reviewing some of the hottest topics relevant to combinatorial chemistry, including solid-phase synthesis of natural product derivations, synthesis of guanidine, palladium catalyzed C-C bond forming reactions, resin supported capture agents and other reagents, synthesis on pins, and monitoring of supporting reactions using IR.

Contents:

1 Solid-Phase Syntheses of Guanidines / Kevin Burgess, Jiong Chen 1

1.2. Outline of Some Solution-Phase Approaches to Guanidines 2

1.3. Solid-Phase Syntheses Involving Resin-Bound Electrophiles 8

1.4. Solid-Phase Syntheses Involving Electrophiles in Solution 14

1.5. Other Supported Guanidines 18

2 Palladium-Catalyzed Carbon-Carbon Bond Formation on Solid Support / Matthew H. Todd, Chris Abell 25

2.2. Heck Reaction 27

2.3. Stille Reaction 45

2.4. Suzuki Reaction 48

2.5. Miscellaneous Reactions 67

3 Benzofused Heterocycles Via Solid-Phase S[subscript N]AR Reactions / Matthias K. Schwarz, Mark A. Gallop 81

3.2. Formation of [6,7]- and [6,8]-Fused Systems 84

3.3. Formation of [6,6]-Fused Systems 97

3.4. Formation of [6,5]-Fused Systems 105

4 Solid-Phase Synthesis of Sequence-Specific Phenylacetylene Oligomers / Jeffrey S. Moore, David J. Hill, Matthew J. Mio 119

4.2. Strategies 120

4.3. Synthetic Tactics 122

4.4. Illustrative Applications 128

4.5. Scope and Limitations 138

4.7. Representative Procedures 140

5 Polymer-Assisted Solution-Phase Methods for Chemical Library Synthesis / Daniel L. Flynn, Rajesh V. Devraj, John J. Parlow 149

5.2. Reactant Sequestration 152

5.3. Byproduct Sequestration 156

5.4. Solution-Phase Derivatization to Facilitate Polymer-Assisted Sequestration 157

5.5. Soluble Bifunctional Reagents 160

5.6. Polymer-Supported Substrates 162

5.7. Polymer-Supported Reagents 165

5.8. Polymer-Supported Catalysts 168

5.9. Polymers for Reaction Quenching/Workup 173

5.10. Combinations of Solid- and Solution-Phase Techniques in Organic Synthesis 175

5.11. Multistep/One-Chamber Solution-Phase Synthesis 182

5.12. Polymer-Assisted Technologies in Multistep Solution-Phase Syntheses 183

6 Solid-Phase Organic Synthesis on Radiation-Grafted Polymer Surfaces: Application of Synphase Crowns to Multiple Parallel Syntheses / Ian W. James, Geoffrey Wickham, Nicholas J. Ede, Andrew M. Bray 195

6.1. Multiple Parallel Syntheses of Individual Compounds 195

6.2. Synthetic Applications of Synphase Crowns 200

6.3. Linker Development Using Synphase Crowns 208

6.4. Tagging Methods for Identifying Individual Crowns 211

6.5. Future Developments 214

7 Vibrational Spectroscopy for Optimization of Solid-Phase Organic Syntheses / Bing Yan 219

7.2. Spectroscopic Methods Applicable to Different Sample Sizes 221

7.3. Optimization in Solid-Phase Organic Syntheses 224

8 Recent Advances in Solid-Phase Synthesis of Natural Products / Lawrence J. Wilson 247

8.2. Prostaglandins 248

8.3. Epothilone a 251

8.4. (S)-Zearalenone 253

8.5. DL-Muscone 255

8.6. Taxoid Libraries from Baccatin III 256

8.7. Sarcodictyin Libraries 258

8.8. Lavendustin A 258

8.9. Indolyl Diketopiperazines 260

8.10. Balanol Analogs 261

8.11. Pseudoalkaloids from Shikimic Acid 263.

Notes:

Includes bibliographical references and index.

ISBN:

0471318256

OCLC:

41299344