ORGANIC SYNTHESIS

ORGANIC SYNTHESIS

COURSE OBJECTIVES:

• To understand the various organic reactions and reagents as tools for the synthesis of organic compounds.
• To learn the principles of protecting group chemistry and retro synthetic approach towards organic synthesis.

LEARNING OUTCOMES:

After the completion of the course, students will be able to –

·         To understand the various organic reactions

• To learn about the modern synthetic method and reagent.
• To introduce the basic concept to retrosynthetic analysis, protecting group chemistry,biosynthesis and biomimetic synthesis.
• To learn about the construction of carbocyclic and heterocyclic ring system.
• To learn how to write reaction mechanisms.
• Be able to apply concepts associated with these general reaction types to product prediction, synthesis design, and reaction mechanism.
  

  Module 1:

   Modern SyntheticMethods

   

  • Baylis-Hillman reaction – Henry reaction – Nef reaction – Kulinkovich reaction – Ritter reaction – Sakurai reaction – Tishchenko reaction –  Brook rearrangement – Tebbeolefination –  Metal mediated C-C and C-X coupling reactions: Heck –Stille – Suzuki – Miyaura – Negishi, Sonogashira – Nozaki-Hiyama-Kishi – Buchwald-Hartwig -Ullmann and Glaser coupling reactions. Click reactions (Huisgen 1,3-dipolaraddition).
  • Multicomponent reactions-Ugireaction,Passerini reaction and Biginellireaction.

  Module 2 :

  SyntheticReagents

   

  3.1. Hydride transfer reagents from Group III and Group IV in reductions – LiAlH₄, DIBAL-H, Red-Al, NaBH₄ and NaCNBH₃ -selectrides, trialkylsilanes and trialkylstannane. Aluminum isopropoxide (oxidation and reduction).Reagents such as NBS – DDQ and DCC.Gilmann reagent – DMAP-Borane, PCC,DEAD (Mitsunobureaction).

  Module 3:

  Construction of Carbocyclic and HeterocyclicRingSystems

   

  • Synthesis of four, five and six-membered rings – photochemical approaches for the synthesis of four membered rings-oxetanes and cyclobutanes – ketene cycloaddition (inter and intra molecular) – Pauson-Khand reaction -Volhardtreaction – Bergman cyclization – Nazarovcyclization – cation-olefin cyclization and radical-olefin cyclization.
  • Inter-conversion of ring systems (contraction and expansion) -Demjenov reaction – Reformatsky reaction. Construction of macrocyclic rings-ring closing metathesis (Grubb’scatalyst).
  • Formation of heterocyclic rings: 5-membered ring heterocyclic compounds with one or more than one hetero atom like N, S or O – pyrrole – furan – thiophene – imidazole – thiazole -oxazole.