Professional Documents
Culture Documents
1. Table S1. Using curved arrows for retrosynthetic analysis: ten examples
2. Table S2. Example retrosynthesis problems and solutions
Table S1. Using curved arrows for retrosynthetic analysis: ten examples
No.
Forward
reaction
Reverse mechanism
Stepwise algorithm
Carbonyl condensations
Aldol
condensation B
H
O
H
O
Aldol
dehydration
HO
H
RO
3
H
B
OH
OH
RO
Claisen
RO
condensation
O
RO O
RO
H
RO
RO
Michael
condensation
RO
RO
H
O
H
RO
RO
Carbonyl addition
5
Hydride
reduction or
Grignard
addition
BH
H
O
R'
H
R
R'
R'
R'
c
H
R'
O
NaBH4
c
R
R'
O
c
R'
RMgBr
R'MgBr
Other additions
6
Diels-Alder*
H3C
H3C
Reductive
amination
Wittig
H
H3C
CH3
F
H
O
a
PPh3
H2N
PPh3
H2O
c
CH3
BH
H3C
NaBH4
PPh3
b
B
H
c
H
B
PPh3
Nucleophilic substitution
9
Acetylide
Substitution#
B
a
RCH2
CH
B
C
RCH2
CH
RCH2 H
10
Williamson
ether
synthesis
a
R'CH2
b
R'CH2
O
R
O
R
R'CH2
O
R
References
1.
2.
Smith, J. G. Organic Chemistry, 1st Ed.; McGraw-Hill: New York, 2007; p 593.
Solomons, T. W. G.; Fryle, C. B. Organic Chemistry; 9th ed.; Wiley: Hoboken, 2007; p 348.
:B
H
HB
O
CH3
CH3
CH3
MgBr
1.PhMgBr,ether
H
CH3
Multi-step
2.H3O+
OH
CH3
CH3
BH
O
H3C
H3C
CH3
CH3
H3C
HO
CH3
HO
HO
B
BH
H3C
H3C
CH3
CH3
O
B
H
CH3
H3C
BH
H3C
CH3
O
CH3
CH2
N
+
CH3
1.orga ni cs ol vent,hea t
H3C
2.OH,H2O
CH3
+
CH2
N
H
References
1.
Boeckman, R. K., Jr.; Bershas, J. P.; Clardy, J.; Solheim, B. J. Org. Chem. 1977, 42,
3630-3633: DOI: 10.1021/jo00442a043.
2.
Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc.
1963, 85, 207-222: DOI: 10.1021/ja00885a021.
7