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A topic from the subject of Synthesis in Chemistry.

  • 10 months ago
  • 3 min read
Total Synthesis: Strategies and Tactics
Introduction
  • Definition of total synthesis
  • History and significance of total synthesis

Basic Concepts
RetrosynthesisFunctional group transformationsProtecting groups
Equipment and Techniques
Laboratory equipmentChromatographic techniquesSpectroscopic techniques
Types of Total Synthesis Experiments
  • Target-oriented total synthesis
  • Mechanistic total synthesis
  • Divergent total synthesis

Data Analysis
  • Interpretation of spectroscopic data
  • Calculation of purity
  • Evaluation of reaction yields

Applications of Total Synthesis
  • Medicinal chemistry
  • Natural product synthesis
  • Materials chemistry

Conclusion
  • Summary of key points
  • Future directions in total synthesis

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Total Synthesis Experiment: Synthesis of Paclitaxel

Objective: To demonstrate the principles and strategies of total synthesis through the stepwise construction of the complex natural product paclitaxel.


Materials:
Taxol precursors (10-deacetyl baccatin III, 7-epi-taxol) Palladium catalyst (Pd(0))
Triphenylphosphine (PPh3) Acetonitrile (CH3CN)
Triethylamine (Et3N) Sodium hydride (NaH)
Procedure:
Step 1: Heck Reaction for Side Chain Assembly

  • Mix taxol precursor 10-deacetyl baccatin III with Pd(0) catalyst, PPh3, and CH3CN.
  • Add Et3N and stir the mixture under an atmosphere of nitrogen.
  • Introduce the side chain bromide (7-epi-taxol) and allow the reaction to proceed for several hours.

Step 2: Deprotection and Deoxygenation

  • Remove the protective group from the side chain using NaH in DMF.
  • Deoxygenate the side chain using Lindlar catalyst (Pd-CaCO3) and hydrogen gas.

Step 3: Acylation and Rearrangement

  • Acylate the hydroxyl group with an appropriate acylating agent.
  • Induce a rearrangement reaction to cyclize the side chain.

Step 4: Final Cyclisation and Paclitaxel Isolation

  • Close the final ring system of paclitaxel through a series of intramolecular reactions.
  • Purify the synthesized paclitaxel using chromatography.

Significance:
Demonstrates the strategic planning and stepwise construction of a complex natural product. Highlights the use of Heck reaction for side chain assembly, deprotection techniques, and cyclization reactions.
Provides insights into the synthetic challenges and limitations encountered in total synthesis. Contributes to the advancement of medicinal chemistry and drug development by providing a synthetic route to a potent anticancer agent.

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