224
N. N. Win and H. Morita
O
Ph
O
OH
HO
[1]benzopyran-2one
CH 3 CH 2 CH 2 COCl/AlCl 3 /
CS 2 ,CH 3 NO 2 /reflux
O
Ph
O
OH
HO
O
(CH 3 ) 2 C=CHCH 2 Br/10% KOH/0°C
O
Ph
O
OH
HO
O
221 (mammea A/BC)
Scheme 5 Synthesis of mammea A/BC (221)
O
O
OH
HO
dihydroxy-4propylcoumarin
225 (mammea B/AC cyclo F)
O
O
O
OH
O
2,2,2-trifluoroethanol
10% aq KOH
0 °C, 90 min
222 (mammea B/AC)
O
O
OH
O
HO
prenyl bromide
m-chloroperbenzoic acid
CH 2 Cl 2 , RT, overnight
HO
Scheme 6 Synthesis of mammea B/AC (222) and mammea B/AC cyclo F (225)
N. N. Win and H. Morita
O
Ph
O
OH
HO
[1]benzopyran-2one
CH 3 CH 2 CH 2 COCl/AlCl 3 /
CS 2 ,CH 3 NO 2 /reflux
O
Ph
O
OH
HO
O
(CH 3 ) 2 C=CHCH 2 Br/10% KOH/0°C
O
Ph
O
OH
HO
O
221 (mammea A/BC)
Scheme 5 Synthesis of mammea A/BC (221)
O
O
OH
HO
dihydroxy-4propylcoumarin
225 (mammea B/AC cyclo F)
O
O
O
OH
O
2,2,2-trifluoroethanol
10% aq KOH
0 °C, 90 min
222 (mammea B/AC)
O
O
OH
O
HO
prenyl bromide
m-chloroperbenzoic acid
CH 2 Cl 2 , RT, overnight
HO
Scheme 6 Synthesis of mammea B/AC (222) and mammea B/AC cyclo F (225)