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Elements of Synthesis Planning

Autor R. W. Hoffmann
en Limba Engleză Paperback – 21 ian 2009

În literatura academică dedicată chimiei organice, observăm adesea o fragmentare între învățarea reacțiilor individuale și aplicarea lor strategică în asamblarea moleculelor complexe. Elements of Synthesis Planning vine să completeze exact această lacună, oferind un cadru riguros pentru transformarea unei structuri țintă ipotetice într-un plan de lucru viabil. Descoperim aici o abordare care nu se limitează la inventarierea reacțiilor, ci prioritizează logica din spatele selecției blocurilor de construcție și a secvențelor de reacție optime.

Subliniem faptul că R. W. Hoffmann tratează sinteza ca pe un proces de inginerie moleculară, unde eficiența este dictată de modul în care sunt gestionate grupurile funcționale și centrele stereogene. Structura volumului reflectă o progresie logică: de la seturi de legături orientate pe schelet și grupuri funcționale, până la utilizarea strategică a grupelor protectoare și ierarhizarea planurilor de sinteză. Un aspect distinctiv este includerea capitolului despre sinteza asistată de calculator, reflectând tranziția domeniului către metodele moderne de analiză. Găsim în această ediție din 2009 și o secțiune valoroasă de soluții la problemele propuse, transformând textul dintr-o expunere teoretică într-un instrument de lucru activ.

În contextul operei autorului, această lucrare reprezintă o evoluție spre sistematizarea pedagogică, spre deosebire de alte contribuții din portofoliul Springer, precum Der Boden in Seiner Chemischen und Biologischen Beschaffenheit, care explorează chimia în contexte istorice sau naturale. Cartea reprezintă o alternativă viabilă la A Holistic Approach to Organic Synthesis de Philip Garner pentru cursurile de chimie organică avansată, cu avantajul unei structuri mai analitice, axate pe ierarhizarea planurilor de sinteză și pe rezolvarea de probleme specifice.

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Specificații

ISBN-13: 9783540792192
ISBN-10: 3540792198
Pagini: 240
Ilustrații: X, 227 p. 297 illus.
Dimensiuni: 155 x 235 x 13 mm
Greutate: 0.41 kg
Ediția:2009
Editura: Springer
Locul publicării:Berlin, Heidelberg, Germany

Public țintă

Graduate

De ce să citești această carte

Recomandăm această carte studenților de la masterat și doctorat care doresc să stăpânească arta planificării sintezei organice. Dincolo de memorarea reacțiilor, cititorul câștigă capacitatea de a descompune logic molecule complexe și de a evalua critic diferite rute sintetice. Este un instrument esențial pentru oricine dorește să treacă de la execuția de laborator la proiectarea autonomă a secvențelor sintetice, beneficiind de expertiza clară a lui R. W. Hoffmann.


Descriere scurtă

Synthesis is at the core of organic chemistry. In order for compounds to be studied—be it as drugs, materials, or because of their physical properties— they have to be prepared, often in multistep synthetic sequences. Thus, the target compound is at the outset of synthesis planning. Synthesis involves creating the target compound from smaller, readily available building blocks. Immediately, questions arise: From which bui- ing blocks? In which sequence? By which reactions? Nature creates many highly complex “natural products” via reaction cascades, in which an asso- ment of starting compounds present within the cell is transformed by speci c (for each target structure) combinations of modular enzymes in speci c - quences into the target compounds [1, 2]. To mimic this ef ciency is the dream of an ideal synthesis [2]. However, we are at present so far from - alising such a “one-pot” operation that actual synthesis has to be achieved via a sequence of individual discrete steps. Thus, we are left with the task of planning each synthesis individually in an optimal fashion. Synthesis planning must be conducted with regard for certain speci - tions, some of which are due to the structure of the target molecule, and some of which relate to external parameters such as costs, environmental compatibility, or novelty. We will not consider these external aspects in this context. Planning of a synthesis is based on a pool of information regarding chemical reactions that can be executed reliably and in high chemical yield.

Cuprins

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.

Recenzii

From the reviews:
“The text is recommended for those with a strong foundation in organic chemistry. … The book would be quite helpful for those who plan syntheses on a regular basis … . The text is a useful addition to the library of any synthetic organic chemist or to select undergraduate and graduate curricula. … Readers will certainly learn more about the chemistry, the logic, and the art of planning a novel synthesis and contributing to a vast and interesting field.” (Bridget G. Trogden, Journal of Chemical Education, Vol. 88, 2011)
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 chemistrytextbooks. 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

Caracteristici

The subject is treated in a concise, focussed manner to keep the book short Needed by every organic chemist Includes problems and solutions Extended list of references included Includes supplementary material: sn.pub/extras