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O
O
O
O
H
2
N
O
O
R
O
O
NH
OH
R
(CF
3
CO)
2
O
H
N
O O
O
O
O
O
O
O
N
O
O
O
N
O
+
+
O
O
O
O
N
N
N
N
N
OCOCF
3
N
N
N
N
Scheme 5-12
12b-allyldeoxoartemisinin 129 (R
¼
CH
2
CH
¼
CH
2
) and related compounds in
high stereoselectivity (Scheme 5-13).
177,178
The most active compound 12b-n-pro-
pyldeoxo-artemisinin, 129 (R
¼
CH
2
CH
2
CH
3
), proved to be as active and toxic as
arteether.
Recently they synthesized more 12-alkyldeoxoartemisinins (Scheme 5-13)
according to this method. Compound 129 [R
¼
b-CH
2
CH(OH)Et, b-CH
2
CH(OH)-
Bu(t)] showed five to seven times greater activity in vitro than qinghaosu.
179
OO
OO
O
O
R = CH
2
CH=CH
2
, CH=CH
2
, CH
2
CH
2
CHO
CH
2
CHO, CH
2
COR′, CH
2
CH(OH)R′,
CH
2
CH(OH)CF
3
, CH
2
COPh, CN,
C
2
H
5
, C
3
H
7
, C
4
H
9
,
O
O
OH
OAc
98
128
O
TiCl
4
BF
3
⋅
Et
2
O
O
O
O
OO
,
,
O
O
O
R
129
Scheme 5-13
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