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MODERN ORGANIC SYNTHESIS Mr. Anand S Burange, Institute Of Chemical Technology, Matunga,...
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MODERN ORGANIC SYNTHESISMODERN ORGANIC SYNTHESISMr. Anand S Burange,Institute Of Chemical Technology, Matunga , Mumbai-400019E-mail: [email protected]
O
OHHO
OH
O
OOH
HO OH
O
OOH
OH
OH
O
OO
OH
OH
HO
OOH
OHHO
O
OOH
HO
HO
O
HO
O
HO
H
N
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Sir, Robert Boyle ; First
man who independently
started working in
scientific field of
chemicals now termed as
Chemistry.
In 1828, when F. Wohler
accidently got urea in the
laboratory, from that day
Organic Chemistry came
into an existence
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WHAT IS A CHEMICAL REACTION?WHAT IS A CHEMICAL REACTION?
Chemical reaction is an effective interaction between two or more molecules/atoms /ions leading to the formation of new compound(s).
A B
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SynthesisOrganic synthesis is a construction of complex organic compounds by a series of chemical reactions.
There are two main areas of research in the field of organic synthesis, namely total synthesis and methodology.
HO
H
H
H
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Three main keys in organic synthesis
O
HO
O
HO
H
N
H
O
H
O
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Functional group InterconversionsFunctional group Interconversions
O
O
O
OH
O
O
O
i
ii
iii
iv
v
vi
vii
I. (CH3 )2S+CH2- (DMSO,NaH,Me3S+ )
II. NaBH4/ EtOH
III. Zn-Hg/ HCl OR N2H4 / KOH
IV. SeO2
V. (a) NaBH4/ EtOH (b) H+ /Heat
VI. NaOH
VII. LDA, PhSeBr/H2O2
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i
ii
iii
iv
v
vi
vii
CHO
CH2OH
COOH
O
OH
O
OH
CHO
NO2
i. NaOH (Cannizaro) OR H- donor reductant
ii. K2Cr2O7/H+ OR KMnO4/H
+
iii. CH2N2 OR (a) KMnO4/H+ (b) 2eq.
MeLi
iv. (a) KMnO4/H+ (b) SOCl2 (c) EtMgBr
v. RhCl(Pph3)3 : Wilkinson’s catalyst
vi. NaCN/EtOH
vii. Conc. HNO3/Conc. H2SO4
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i
ii
iii
iv
v
vi
vii
O
OH
O
O
O
O
OH
i. CH2I2, Zn(Cu)/ Et2O
ii. m-CPBA (Bartlett Mechanism)
iii. SeO2
iv. (a) SeO2 (b) MnO2
v. (a) SeO2 (b) MnO2 (c) -CH2 –SOMe2
vi. (a) SeO2 (b) MnO2 (c)H2O2/OH-
vii. (a) HBr (b) Mg /Dry ether (C) Ph-CHO
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i
ii
iii
iv
v
vi
vii
O
O
O
O
CHO
OH
HO
O
CO2Et
NH
O
i. m-CPBA
ii. CH2N2
iii. (a) Cl-CH2-COOEt/Me3CONa (b) H3O+ OR Ph3P=CH-OMe
iv. (a)Mg-Hg/ TiCl4 (b) H2O
v. (a) H2N-OH (b) H+
vi. (a)Pyrrolidine/TsOH (b) CO (OEt)2
vii. Ph3P=CH2
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Some Functional group Interconversions for practiceSome Functional group Interconversions for practice
H
O HO
i. 9-BBNii. Ethanolamine
OHNH2 i. Cl-PO(OEt)2/NaH
ii. NaNH2/NH3 (Via Benzyne)
OH
OH
i. Hg(OAc)2 /H2Oii. NaBH4/ OH-
i. B2H6/ solventii. H2O2/ OH-
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Asymmetric SynthesisAsymmetric Synthesis
OH
OH
OH
OH
OsO4 OR KMnO4
I2/AgOAc (dry) OR (a)m-CPBA (b) Hydrolysis
Alkene dihydroxylation
O
O
NaBH4
NaBH4
CeCl3
OH
OH
Reduction
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Luche’s Reduction
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CO2Me
CO2Me
Stereospecific cycloaddition reactions
CO2Me
CO2Me
MeO2C
CO2Me
CO2Me
CO2Me
[4+2] cycloaddition reactions takes place in presence of heat
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O O
Epoxidation
m-CPBAi. NBSii. OH-
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GETTING SLEEPYNOW IT’S TIME TO MOVE YOUR HEAD UP & DOWN
!!ANTI PERIPLANAR RELATIONSHIP!!
iPr
Cl
MeRO-
?
iPr
Cl
Me
H
iPr
Cl
Me
HRO-
iPr Me
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OH
TsO(CH3)3O-
NH2OH
HNO2
OH
NH2
HNO2
NH2OH
HNO2
O
CHO
O
O
DON’T GET FRUSTRATED!!!
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Retrosynthesis – thinking backwards from relatively complex molecules to simpler ones – the disconnection approach originated by E.J. Corey (Nobel Prize 1990)
Terms involvedTarget Molecule (TM) The compound we wish to prepare
Retrosynthetic Analysis The process of WORKING BACKWARDS from the TM in order to devise a suitable synthetic route.
Readily Available Starting Materials (RASM) cheap, commercially available compounds.
Synthon An idealised fragment, usually a cation or anion, resulting from a disconnection.
Synthetic Equivalent The actual compounds used to function as synthons.
Functional Group Interconversion (FGI) The process of writing one functional group for another to help synthetic planning and to help
disconnection.
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O
Target MoleculeO
C-C dix O
Synthons
OO
Cl+ AlCl3 Friedel Craft's reagent
Chemical Equivalents (C.E.)O
Cl+ AlCl3
O
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NR2
NO2O2N
CF3
NR2
NO2O2N
CF3
C-N dix
Cl
NO2O2N
CF3
C-N dix
Cl
CF3
TM (Target Molecule)
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Cl
CF3
1. Conc.HNO3/conc.H2SO4
2. R2NH/Base
NR2
NO2O2N
CF3
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