Organic Synthesis : The Disconnection Approach

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  • Edition: 2nd
  • Format: Paperback
  • Copyright: 2008-12-31
  • Publisher: Wiley

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Organic Synthesis: The Disconnection Approach is the long-awaited second edition of a classic textbook; the first to provide a structured course in retrosynthesis- now an important technique used by generations of organic chemists. Now fully revised and updated with a modern look, 25 years of advances in organic synthesis are reflected with the addition of new examples and synthetic pathways. Additional material has been added to take the student to the level required by the bestselling sequel, "Organic Synthesis: Strategy and Control" and the later chapters have extensive new material based on courses that the authors give to chemists in the pharmaceutical industry.

Table of Contents

Prefacep. ix
General Referencesp. xi
The Disconnection Approachp. 1
Basic Principles: Synthons and Reagents Synthesis of Aromatic Compoundsp. 7
Strategy I: The Order of Eventsp. 17
One-Group C-X Disconnectionsp. 23
Strategy II: Chemoselectivityp. 29
Two-Group C-X Disconnectionsp. 35
Strategy III: Reversal of Polarity, Cyclisations, Summary of Strategyp. 45
Amine Synthesisp. 53
Strategy IV: Protecting Groupsp. 61
One Group C-C Disconnections I: Alcoholsp. 69
General Strategy A: Choosing a Disconnectionp. 77
Strategy V: Stereoselectivity Ap. 83
One Group C-C Disconnections II: Carbonyl Compoundsp. 93
Strategy VI: Regioselectivityp. 101
Alkene Synthesisp. 107
Strategy VII: Use of Acetylenes (Alkynes)p. 115
Two-Group C-C Disconnections I: Diels-Alder Reactionsp. 121
Strategy VIII: Introduction to Carbonyl Condensationsp. 129
Two-Group C-C Disconnections II: 1,3-Difunctionalised Compoundsp. 133
Strategy IX: Control in Carbonyl Condensationsp. 139
Two-Group C-C Disconnections III: 1,5-Difunctionalised Compounds Conjugate (Michael) Addition and Robinson Annelationp. 151
Strategy X: Aliphatic Nitro Compounds in Synthesisp. 161
Two-Group Disconnections IV: 1,2-Difunctionalised Compoundsp. 167
Strategy XI: Radical Reactions in Synthesisp. 177
Two-Group Disconnections V: 1,4-Difunctionalised Compoundsp. 185
Strategy XII: Reconnectionp. 193
Two-Group C-C Disconnections VI: 1,6-diCarbonyl Compoundsp. 199
General Strategy B: Strategy of Carbonyl Disconnectionsp. 207
Strategy XIII: Introduction to Ring Synthesis: Saturated Heterocyclesp. 217
Three-Membered Ringsp. 229
Strategy XIV: Rearrangements in Synthesisp. 237
Four-Membered Rings: Photochemistry in Synthesisp. 245
Strategy XV: The Use of Ketenes in Synthesisp. 251
Five-Membered Ringsp. 255
Strategy XVI: Pericyclic Reactions in Synthesis: Special Methods for Five-Membered Ringsp. 261
Six-Membered Ringsp. 269
General Strategy C: Strategy of Ring Synthesisp. 279
Strategy XVII: Stereoselectivity Bp. 289
Aromatic Heterocyclesp. 301
General Strategy D: Advanced Strategyp. 313
Indexp. 325
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