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O O
O
O
O O
O O
F/CF
3
O
O
O
98
O
O
O
O
OH
O
O
F/CF
3
O
O
Scheme 5-14
O'Neill et al. synthesized 12-C ethanol of deoxoartemisinin and its ethers and
esters (Scheme 5-14). The selected derivatives were generally less potent than
the dihydroartemisinin in vivo test.
180
Posner et al. synthesized some C-glycosides (Scheme 5-15) by using 12-F-
deoxoartemisinin as the intermediate.
181,182
These compounds had high antimalar-
ial potencies in vitro against Plasmodium falciparum. Some were active in vivo, but
less than arteether.
At the beginning of the 1990s, dihydroartemisinin acetate 128, as an electrophi-
lic
reagent,
was
reacted
with
aromatic
substrates
in
the
presence
of
boron
O O
O O
98
O
O
O
O
F
R
CCPh
CCC
6
H
13
,
C
C
SiMe
3
R= Me, Et,
,
OMe
R
′
O
MeO
OR
′
OMe
MeO
OMe
Me
R
′
N
N
O
S
R
′
Scheme 5-15
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