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