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Dead Ends and Detours

  • ID: 2179521
  • Book
  • 290 Pages
  • John Wiley and Sons Ltd
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A plethora of publications provide valuable information for the organic chemist, yet the results are almost always based on successful reactions. However, a chemist′s life is unfortunately not that easy. On the contrary, trial and error is still one of the most commonly used methods. Thus it would be useful to have access to those syntheses that do not work, since they also provide important results of great importance for further synthesis.

This long–awaited book by M. A. Sierra and M. C. de la Torre fills just such a gap. Using major total syntheses they explain the most varied problems and recommend ways out of such dilemmas: Problems at the start and end of a synthesis, difficult and unexpected reactivities of functional groups, problems due to steric properties and much more.

The result is a true wealth of information for any organic chemist. The essential tool for successful total synthesis.
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Chapter 1: Introduction: From the Paper to the Laboratory.


Chapter 2: Tuning–up, Tactical and Strategic Changes.

2.1 Tuning–up Reaction Conditions.

2.2 Tactical Changes.

2.3 Strategic Changes.


Chapter 3: Working with Models.

3.1 (–)–Stenine.

3.2 (+)–Piperazinomycin.

3.3 (+)–Damavaricin D.

3.4 Dynemicin A.


Chapter 4: The Unexpected Reactivity or Inertia of Common Functional Groups.

4.1 Pseudotabersonine.

4.2 Octalactins A and B.

4.3 (–)–Polycavernoside A.


Chapter 5: The Influence of Remote Substituents.

5.1 "Alive" Dead Steric Volume.

5.2 The Reactive Remote Group.


Chapter 6: The Elusive Side Chain.

6.1 (±)–Scopadulcic Acid B.

6.2 Dysidiolide.

6.3 (+)–Epoxydictymene.

6.4 (±)–Lepadiformine.


Chapter 7: The Unpredictable Stereochemistry.

7.1 Nocardiones A and B.

7.2 (±)–Breynolide.

7.3 Hamigerans A and B.

7.4 Calphostin A.

7.5 Fragment C3–C10 of Cytovaricin.

7.6 Goniocin.


Chapter 8: Reluctant Ring Closures.

8.1 Discorhabdin C.

8.2 Discorhabdin A.

8.3 Frondosin B.

8.4 (–)–Laulimalide.

8.5 ent–Rubifolide.

8.6 Roseophilin Tricyclic Core: The Formal Total Synthesis of Roseophilin.

8.7 (–)–Papuamine.


Subject Index.
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Miguel A. Sierra
Maria C. de la Torre
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