CH 588 : Organic Synthesis


  • Strategy and design of organic synthesis: Introduction, scope and a brief history of organic synthesis, synthetic strategy, retro-synthesis, analysis and practice of total synthesis, linear and convergent synthesis.
  • Concepts of synthetic equivalents and Umpolung: benzoyl and acyl anion equivalents, dithianes, enol ethers and nitro compounds.
  • Carbon-Carbon bond formation: alkylation of enolates, enamines and hydrazones, alkylation of heteroatom stabilized anions, organometallic reagents.
  • Carbon-Carbon double bond formation: aldol condensation, Wittig and related reactions, Peterson olefination, Julia-Lythgoe olefination, carbonyl coupling reaction (McMurry reaction), Tebbe reagent, Shapiro and related reactions, b-elimination and dehydration, From diols and epoxides, from acetylenes, from other alkenes (olefin metathesis and transition metal catalyzed cross coupling reactions).
  • Carbon-Carbon triple bond formation: from other acetylenes, from carbonyls, from olefins, from strained rings, Eschenmosher fragmentation, allenes etc.
  • 3-Membered rings: Epoxides- using peracids, hydroperoxides and dioxiranes; transition metal catalyzed epoxidation, halohydrins, Darzen’s condensation, sulfur ylides.
  • Cyclopropanes-Simmons Smith reaction, diazo compounds, sulfur ylides and SN2 displacements. Aziridines-nitrenes and SN2 displacements.
  • 4-Membered rings: Various methods of forming cyclobutanes, cyclobutenes and oxetanes
  • 5-Membered rings: intramolecular SN2 reactions, intramolecular Michael and aldol condensation reactions, intramolecular Wittig olefination, ring expansion and contraction reactions, 1,3-dipolar cycloaddition reactions, Nazarov cyclization, arene-olefin photocycloaddition, radical cyclization reactions.
  • 6-Membered rings: Diels-Alder reaction, o-quinodimethanes, cation olefin cyclization, Robinson annulations
  • Biosynthesis: biogenesis and biosynthesis; biosynthetic pathways of some mono, sesqui and diterepenes and steroids.
  • Selected synthesis of natural products: Total synthesis of several triquinanes, platensimycin, perhydrohistrionicotoxin, progesterone, estrone, prostaglandins, cubane, taxol and epothilones.

Text References

  1. David J. Hart “Organic Synthesis via Examination of Selected Natural Products” World Scientific, 2011
  2. S. Warren, “Designing Organic Syntheses”, John Wiley & Sons 2009.
  3. G. S. Zweifel and M. H. Nantz. “Mdern Organic Synthesis-An Introduction”,W. H. Freeman and Company, 2006.
  4. R. O. C. Norman and J. M. Coxon “Principles of Organic Synthesis” Nelson Thornes, Third Edition, 2005.
  5. Michael B. Smith and Jerry March, “March’s Advanced Organic Chemistry”, Fifth Ed., Wiley, 2001.
  6. K. C. Nicolaou, E. J. Sorenson, “Classics in Total Synthesis, I, II and III”
  7. B. M. Trost and I. Fleming, “Comprehensive Organic Synthesis”, Pergamon Press, 1992.
  8. T.W. Greene, “Protecting Groups in Organic Synthesis” (3rd edition), J. Wiley & Sons, 1999.
  9. F. A. Carey, R. Sundberg, , “Advanced Organic Chemistry, Part B”, 2nd Ed., Plenum Press, 1990.
  10. E. J. Corey, X. Cheng, “The Logic of Chemical Synthesis”, John Wiley 1989.
  11. W. Carruthers, “Some Modern Methods in Organic Synthesis”, Cambridge University Press 1989.
  12. S. Warren, “Organic Synthesis: The Disconnection Approach”, John Wiley & Sons.