Elements of Synthesis Planning - Hoffmann, Reinhard W.

Reinhard W. Hoffmann 

Elements of Synthesis Planning

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Elements of Synthesis Planning

The total synthesis of compounds with interesting physical or biological properties is at the core of organic chemistry. Since only a small number of such compounds originate from natural sources, devising de novo routes to unique and artificial scaffolds requires the skills of planning and executing multi-step syntheses and having a toolbox of methodologies at one s disposal. Often, even the best plans require modifications, fine-tuning or entire rerouting, and chemists are faced with the daily challenge of choosing the right combination of reagents and building blocks for a whole set of problems: Which building blocks are optimal? In which sequence should they be assembled? Which reactions accomplish the task best?
This text focuses on these basic considerations that govern the planning and execution of a synthesis. The author details synthetic strategies, provides criteria for ranking different synthesis plans, and provides guidelines for optimizing syntheses. References to the original work provide the reader with a means of further study of the details and original considerations. The text takes a more in-depth look at synthesis than do standard organic chemistry textbooks and is a useful complement to other books on the market.
Furthermore it includes problems and solutions.


Produktinformation

  • Verlag: Springer, Berlin
  • 2009
  • Ausstattung/Bilder: 2009. XII, 230 p. w. 280 draw.
  • Best.Nr. des Verlages: 12201204
  • Englisch
  • Abmessung: 239mm x 157mm x 14mm
  • Gewicht: 365g
  • ISBN-13: 9783540792192
  • ISBN-10: 3540792198
  • Best.Nr.: 23894060
From the reviews: " From an undergraduate learning perspective the concept of synthesis planning or retrosynthesis can appear to be a daunting prospect. The idea of being asked to think backwards for many is a big leap, despite the vast majority already possessing a well-stocked chemical toolbox and being more than capable to explain a multitude of complex mechanistic transformations. In Elements of synthesis planning, a reworked translation of his original German text, Reinhard Hoffmann sets out to 'demystify' the art of synthetic planning, which is an essential and vital skill practised every day throughout the worldwide organic chemistry community. In 12 clear and logical chapters, Hoffmann takes the reader from the basic concepts of retrosynthesis (use of synthons, identifying key bond disconnections, unmasking symmetry elements etc) to dedicated chapters on the application of chiral building blocks, strategic planning of complex synthetic sequences and the synthesis of polycyclic ring systems. In the final chapter, all these concepts are brought together to elegantly compare several individual approaches to one of five representative natural products, highlighting the tactics and strategies employed. As such, this text would ideally complement an advanced undergraduate course on complex organic synthesis, which is beyond the level of most standard organic chemistry textbooks. It would also prove highly useful to postgraduates at the beginning of their research careers in synthesis to inspire creativity and maybe put their ideas into practice. Gordon Florence , Chemistry World, 2009, 6(8), p. 63 Aus den Rezensionen: "... Didaktisch geschickt führt der Autor in die Prinzipien der retrosynthetischen Analyse ein; dabei ist die pragmatische Unterteilung in die Abschnitte 'Functional Group Oriented Bond-Sets', 'Skeleton Oriented Bond-Sets' und 'Building Block Oriented Bond-Sets' äußerst sinnvoll. ... Dann stellt das Buch eine Reihe von Synthons exemplarisch vor. ... Am Ende eines jeden Kapitels erhält der Leser Aufgaben, für die am Ende des Texts eine Lösung steht. ... Es ist ein guter Einstieg für all diejenigen, die einschlägige Erfahrungen in organischer Synthese besitzen ..." (Dieter Hoppe, in: Nachrichten aus der Chemie, March/2010, Vol. 58, Issue 3, S. 379)

From the reviews: " From an undergraduate learning perspective the concept of synthesis planning or retrosynthesis can appear to be a daunting prospect. The idea of being asked to think backwards for many is a big leap, despite the vast majority already possessing a well-stocked chemical toolbox and being more than capable to explain a multitude of complex mechanistic transformations. In Elements of synthesis planning, a reworked translation of his original German text, Reinhard Hoffmann sets out to 'demystify' the art of synthetic planning, which is an essential and vital skill practised every day throughout the worldwide organic chemistry community. In 12 clear and logical chapters, Hoffmann takes the reader from the basic concepts of retrosynthesis (use of synthons, identifying key bond disconnections, unmasking symmetry elements etc) to dedicated chapters on the application of chiral building blocks, strategic planning of complex synthetic sequences and the synthesis of polycyclic ring systems. In the final chapter, all these concepts are brought together to elegantly compare several individual approaches to one of five representative natural products, highlighting the tactics and strategies employed. As such, this text would ideally complement an advanced undergraduate course on complex organic synthesis, which is beyond the level of most standard organic chemistry textbooks. It would also prove highly useful to postgraduates at the beginning of their research careers in synthesis to inspire creativity and maybe put their ideas into practice. Gordon Florence , Chemistry World, 2009, 6(8), p. 63 Aus den Rezensionen: ... Didaktisch geschickt führt der Autor in die Prinzipien der retrosynthetischen Analyse ein; dabei ist die pragmatische Unterteilung in die Abschnitte Functional Group Oriented Bond-Sets , Skeleton Oriented Bond-Sets und Building Block Oriented Bond-Sets äußerst sinnvoll. ... Dann stellt das Buch eine Reihe von Synthons exemplarisch vor. ... Am Ende eines jeden Kapitels erhält der Leser Aufgaben, für die am Ende des Texts eine Lösung steht. ... Es ist ein guter Einstieg für all diejenigen, die einschlägige Erfahrungen in organischer Synthese besitzen ... (Dieter Hoppe, in: Nachrichten aus der Chemie, March/2010, Vol. 58, Issue 3, S. 379)

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Inhaltsangabe

Introduction.- Functional Group Oriented Bond-Sets.- Skeleton Oriented Bond-Sets.- Building Block Oriented Synthesis.- The Basis for Planning.- Formation of Cyclic Structures.- Protecting Groups.- Ranking of Synthesis Plans.- Computer-Aided Synthesis Planning.- Stereogenic Centers and Planning of Syntheses.- Enjoying the Art of Synthesis.- Summary and Concluding Remarks.- Solutions to Problems.