Solid-Phase Organic Synthesis

by Burgess, Kevin

• ISBN13: 9780471318255
• ISBN10: 0471318256
• Edition: 1st
• Format: Hardcover
• Copyright: 1999-12-14
• Publisher: Wiley-Interscience

Summary

Solid-Phase Organic Synthesis Edited by Kevin Burgess, Texas A & M University Efficient, high-throughput chemistry is now the focus of many research laboratories. Solid-phase organic syntheses are central to many of these combinatorial and parallel screening methodologies. Consequently, they have been a major scientific theme of the 1990s and promise to remain prominent for the first part of the new millennium. Indeed, a bewildering number of papers have entered the literature on this topic; some report minor modifications enabling transformation of solution-phase methods to a solid support, while others report major innovations. Solid-Phase Organic Synthesis collects, highlights, and critiques some of the key developments in the field.Leading practitioners explain different perspectives on diverse aspects of the area. Specific topics covered include: Syntheses of guanidines Palladium-catalyzed C-C bond forming reactions S_nAr reactions for the formation of heterocycles Sequence-specific arylalkyne oligomers Resin-supported capture agents and other reagents Synthesis on pins Monitoring of supported reactions using IR Solid-phase syntheses of natural product derivativesOf related interest: Combinatorial Chemistry and Molecular Diversity in Drug Discovery, Eric M. Gordon and James F. Kerwin 1998 (0-471-15518-7) 544 pp. Combinatorial Chemistry Synthesis and Application, Stephen R. Wilson and Anthony W. Czarnik 1997 (0-471-12687-X) 288 pp.

Author Biography

Kevin Burgess FRSC is a British chemist who has been Rachal Professor of Chemistry at Texas A&M University since 2004. He was educated at the University of Bath, the University of East Anglia and Darwin College, Cambridge.

Table of Contents

Preface	xi
Contributors	xiii
Solid-Phase Syntheses of Guanidines	1	(24)
Kevin Burgess
Jiong Chen
Introduction	1	(1)
Outline of Some Solution-Phase Approaches to Guanidines	2	(6)
Solid-Phase Syntheses Involving Resin-Bound Electrophiles	8	(6)
Solid-Phase Syntheses Involving Electrophiles in Solution	14	(4)
Other Supported Guanidines	18	(1)
Conclusion	19	(6)
References	20	(5)
Palladium-Catalyzed Carbon-Carbon Bond Formation on Solid Support	25	(56)
Matthew H. Todd
Chris Abell
Introduction	25	(2)
Heck Reaction	27	(18)
Stille Reaction	45	(3)
Suzuki Reaction	48	(19)
Miscellaneous Reactions	67	(4)
Concluding Remarks	71	(10)
References	71	(10)
Benzofused Heterocycles Via Solid-Phase SNAR Reactions	81	(38)
Matthias K. Schwarz
Mark A. Gallop
Introduction	81	(3)
Formation of [6,7]- and [6,8]-Fused Systems	84	(13)
Formation of [6,6]-Fused Systems	97	(8)
Formation of [6,5]-Fused Systems	105	(3)
Conclusions and Outlook	108	(11)
References	111	(8)
Solid-Phase Synthesis of Sequence-Specific Phenylacetylene Oligomers	119	(30)
Jeffrey S. Moore
David J. Hill
Matthew J. Mio
Introduction	119	(1)
Strategies	120	(2)
Synthetic Tactics	122	(6)
Illustrative Applications	128	(10)
Scope and Limitations	138	(2)
Conclusion	140	(1)
Representative Procedures	140	(9)
References	144	(5)
Polymer-Assisted Solution-Phase Methods for Chemical Library Synthesis	149	(46)
Daniel L. Flynn
Rajesh V. Devraj
John J. Parlow
Introduction	149	(3)
Reactant Sequestration	152	(4)
Byproduct Sequestration	156	(1)
Solution-Phase Derivatization to Facilitate Polymer-Assisted Sequestration	157	(3)
Soluble Bifunctional Reagents	160	(2)
Polymer-Supported Substrates	162	(3)
Polymer-Supported Reagents	165	(3)
Polymer-Supported Catalysts	168	(5)
Polymers for Reaction Quenching/Workup	173	(2)
Combinations of Solid- and Solution-Phase Techniques in Organic Synthesis	175	(7)
Multistep/One-Chamber Solution-Phase Synthesis	182	(1)
Polymer-Assisted Technologies in Multistep Solution-Phase Syntheses	183	(4)
Conclusion	187	(8)
References	188	(7)
Solid-Phase Organic Synthesis on Radiation-Grafted Polymer Surfaces: Application of Synphase Crowns to Multiple Parallel Syntheses	195	(24)
Ian W. James
Geoffrey Wickham
Nicholas J. Ede
Andrew M. Bray
Multiple Parallel Syntheses of Individual Compounds	195	(5)
Synthetic Applications of Synphase Crowns	200	(8)
Linker Development Using Synphase Crowns	208	(3)
Tagging Methods for Identifying Individual Crowns	211	(3)
Future Developments	214	(5)
References	214	(5)
Vibrational Spectroscopy for Optimization of Solid-Phase Organic Syntheses	219	(28)
Bing Yan
Introduction	219	(2)
Spectroscopic Methods Applicable to Different Sample Sizes	221	(3)
Optimization in Solid-Phase Organic Syntheses	224	(17)
Conclusion	241	(6)
References	242	(5)
Recent Advances in Solid-Phase Synthesis of Natural Products	247	(22)
Lawrence J. Wilson
Introduction	247	(1)
Prostaglandins	248	(3)
Epothilone a	251	(2)
(S)-Zearalenone	253	(2)
DL-Muscone	255	(1)
Taxoid Libraries from Baccatin III	256	(2)
Sarcodictyin Libraries	258	(1)
Lavendustin A	258	(2)
Indolyl Diketopiperazines	260	(1)
Balanol Analogs	261	(2)
Pseudoalkaloids from Shikimic Acid	263	(1)
Conclusions	263	(6)
References	264	(5)
Index	269