Strategies and Tactics in Synthetic Medicinal Chemistry Course Resources 

The following articles are intended to supplement material found in the various textbooks and lectures.

Synthesis Planning

  • The Beauty of Synthesis
  • Pattern Recognition in Retrosynthetic Analysis
  • Oxidative Coupling of Enolates, etc.
  • Cyclizations of Alkynes: Revisiting Baldwin’s Rules for Ring Closure
  • Cascade Reactions

Strategies for Aromatic Compounds

  • Palladium-Catalyzed Coupling Reactions
  • Synthesis of Fluotracen
  • Synthesis of a Streptonigrin Model

Protecting Groups

  • Selective Deprotection of Silyl Ethers

Polarity Reversal (Umpolung)

  • (+)-13-Deoxytedanolide Synthesis by Amos Smith

Template and Chelation Effects

  • Olefin Metathesis
  • Olefin Cross-Metathesis
  • The Total Synthesis of the Annonaceous
    Acetogenin 10-Hydroxyasimicin

Stereospecific Synthesis

  • The Mukaiyama Reaction
  • Roush’s Synthesis of Olivomycin A


  • Photochemical Reactions as Key Steps in Natural
    Product Synthesis by Thorsten Bach* and Jorg P. Hehn
  • Schreiber’s Synthesis of Avenaciolide

Synthesis Under Extreme Conditions

  • Modern Strategies in Electroorganic Synthesis
  • High Pressure Synthesis of Hirsutene
  • Electrochemical Synthesis of Alliacol A

Synthesis Using Solid Supports

  • Multi-Step Application of Immobilized Reagents and Scavengers: A Total Synthesis of Epothilone C

Examples of Total Synthesis

    • Sheehan’s Synthesis of Penicillin V
    • Nicolaou’s Synthesis of Amphoteronolide B
    • Corey’s Synthesis of Giberellic Acid
    • Danishefsky’s Synthesis of Gelsemine
    • Yamamoto’s Synthesis of Gambierol
    • Corey’s Synthesis of Ginkolide B
    • Smith’s Synthesis of Jatrophone
    • Trost’s Synthesis of Mycalamide A
    • Smith’s Synthesis of Phorboxazole A
    • Nicolaou’s Synthesis of Taxol