O

CARBOXYLIC ACIDS O R – +
OM
O
R
OH
R Cl
Br

MH, M = Li, Na, K

R NH2

l)2
–H2

OC
1.
O O
+

Br 2
2.

(C
H2
,P
R R

or
CO2 O

O
Br 3

D
Cl
SO
1. H l) 2
N, OC
2. H 3 HO
o r (C N
Et 3
3 +
2 O Cl 2 ,
.S
O OH
2
1
C H 2C
2. R

O R1
O O
Ph3P, DEAD ROH
R O R2 R H3O+, D R OR
OH OH
R1 R2
1.
SO
2. Cl
OH RN
Ar
2
D
EA H
2

P, D

1.
Ph 3
lBN hesis

2.
SO NH 2●
1. SOCl2 or (COCl)2
2. MeNHOMe●HCl

NH
Cl 2
t
yn

or
rs

O
ste

(C
R NR
,A

OC
ne

H 2O
R
nH

O Ar
rto

l) 2
R
3S
Ba
Bu
1.
2.

O
R–CH3 + CO2
R NH
O NH2
R N OMe