Chemistry Reference
In-Depth Information
R
1
R
2
OH
O
1
O
10
4
C
5
H
11
O
O
R
4
R
6
R
2
R
3
R
5
R
1
OH
249a
R
1
=OH, R
2
=R
3
=R
4
=R
5
=R
6
=H
249c
R
1
=R
3
=OH, R
2
=R
4
=R
5
=R
6
=H
249e
R
2
=R
3
=OH, R
1
=R
4
=R
5
=R
6
=H
249g
R
1
=R
6
=OH, R
2
=R
3
=R
4
=R
5
=H
249i
R
2
=R
6
=OH, R
1
=R
3
=R
4
=R
5
=H
249b
R
2
=OH, R
1
=R
3
=R
4
=R
5
=R
6
=H
249d
R
1
=R
4
=OH, R
2
=R
3
=R
5
=R
6
=H
249f
R
2
=R
4
=OH, R
1
=R
3
=R
5
=R
6
=H
249h
R
1
=R
5
=OH, R
2
=R
3
=R
4
=R
6
=H
249j
R
2
=R
5
=OH, R
1
=R
3
=R
4
=R
6
=H
OH
O
R
1
R
2
1
10
4
O
O
C
5
H
11
O
R
2
R
3
R
1
R
4
OH
249a-f
O
OMOM
TMS
O
( )
5
O
HO
D
O
C
9
H
19
OMs
OMOM
OH
F
Cl
C
OMOM
( )
4
O
A
B
O
E
G
O
OH
O
R
1
R
2
1
10
4
O
O
O
C
5
H
11
R
6
R
5
R
2
OH
R
1
249g-i
Scheme 10-43. Parallel fragment assembly strategy for a small library of acetogenin mimics
(Yao et al.).
of mimics with a different tail (Scheme 10-45). Their cytotoxicity toward L1210 is
summarized in Table 10-7. These analogs turned out to be much less cytotoxic than
natural products; among these mimics, mimics with phenyl or piperidine as a side
chain (259b, c, h and 260b, c) showed lower activity than others.
OMOM
OMOM
OH
NaH, DM
F
C
9
H
19
OMs
OMOM
C
9
H
19
O
OMOM
+
HO
OH
OMOM
OMOM
249
248
250
OMOM
O
Cl
O
(1) BuLi, BF
3
.OEt
2
TMS
O
C
9
H
19
O
OMOM
(2) MOMCl
(3) TBAF
NaOH, H
2
O
OMOM
Bu
4
NHSO
4
251
O
OMOM
OMOM
( )
5
O
O
247d
+
C
9
H
19
O
OMOM
O
OMOM
253
252
Scheme 10-44. A representative synthesis of mimics 247a-j.
Search WWH ::
Custom Search