Organic Synthesis I n text : Adv. Org. Syn. (4 th Ed.) Part B, Care : acquiring various reactions and synthetic strategies to design synthetic routes for target molecules Other texts & ref. : a) Designing Organic Synthesis – S. Warren b) Modern Organic Synthesis – D. L. Boger c) Advanced Organic Chemistry – J. March d) Modern Methods of Organic Synthesis (4 th Ed.) – W. Carr e) Organic Synthesis (2 nd Ed.) – J. Furhop, G. Penzlin f) Classics in Total Synthesis I, II – K.C. Nicolaou g) The Logic of Chemical Synthesis – E. J. Corey
Transcript
Organic Synthesis I
1. Main text : Adv. Org. Syn. (4th Ed.) Part B, Carey & Sundberg
2. Aim : acquiring various reactions and synthetic strategies to design synthetic routes for target molecules
3. Other texts & ref. : a) Designing Organic Synthesis – S. Warrenb) Modern Organic Synthesis – D. L. Bogerc) Advanced Organic Chemistry – J. Marchd) Modern Methods of Organic Synthesis (4th Ed.) – W. Carrutherse) Organic Synthesis (2nd Ed.) – J. Furhop, G. Penzlinf) Classics in Total Synthesis I, II – K.C. Nicolaoug) The Logic of Chemical Synthesis – E. J. Corey
The molecular world
moleculesof
value
moleculesfrom
synthesis
synthetic products of
valuedecrease
complexityincrease
complexity
What will be covered in Org. Syn. I
Chapter 1 : Alkylation – carbanionChapter 2 : Reaction of Carbon Nu: w/ carbonylChapter 3 : Functional group interconversionChapter 5 : Reduction of Carbonyl etc.Chapter 7 : Organometallic – main groupChapter 12 : OxidationChapter 13 : Planning and Execution** Named Reactions**** Reaction Mechanism**
Homework : Selected problems from each chapter
ORGANIC SYNTHESIS
TOTAL SYNTHESIS (target oriented)
Method Oriented
Reagent Catalyst Strategy TacticsNaturalProducts
DesignedMolecules
TheoreticallyInterestingMolecules
MedicinallyInterestingMolecules
BiologicallyInterestingMolecules
MateriallyInterestingMolecules
Reaction Mechanism (or reasonably drawn detailed reaction pathway) is important
-- Examples --
OH
O
+ MeOHH2SO4 (cat.)
MeOHO
Oi) esterification
H
O
+ MeOHTsOH (cat.)
CH2Cl2O
Oii) acetals
H
O10%NaOH
Acetone H
HO Oiii) aldol
J. Am. Chem. Soc., 1914, 36, 530
H
O
50%NaOH
water
OH
ONa
O
+
iv) Cannizzaro rxn.
OH
O
H+
OH
OH
esterification
acetals
MeOHOH
OH
HOMe
OH
OH2
OMe
OH
OMe
H+O
OMe
H2O
H
O
H+
H
OH
MeOHH
OH
HOMe
H
OH2
OMe
H
OMe
H2O
MeOHH
HO
OMe
Me
H+
H
O
OMe
Me
H
O
H
OH-
H2O H
Oaldol
H
O
OH-
H
O
OH
Cannizzaro rxn.
H
O
H
O
O O
OH-
H
O
HOH
OH-
H
O
O
O
O
H
O
H
O
H+
Classification of Organic Synthesis
1. Linear Synthesis : tedious, inefficient but could be simple ex.) DNA, Peptide Synthesizer
