Bioactive Compounds from Medicinal Plants in Myanmar
223
19 kbar
CH 2 Cl 2
RT, 3 d
62%
O
O
cinnamaldehyde
1:7.2
+
O
MOMO
MOMO
R
R = OMe or OMOM
MOM:methoxymethyl ether
HCl, MeOH
50°C, 2 h
174 (4-hydroxypanduratin A) R = OH
186 (nicolaioidesin B) R = OMe
O
i) n-BuLi, MOM-bromobenzenes
THF, –78°C;
ii) DMP, CH 2 Cl 2
RT, 2 h
O
OH
OH
R
174: 71%
186: 69%
R
Br
MOMO
MOMO
Scheme 3 Synthesis of 2-hydroxyisopanduratin A (174) and nicolaioidesin B (186)
O
Ph
O
OH
HO
mammeisin
DDQ
benzene, RT, 2 h
220 (mammea A/AA cyclo D)
O
O
Ph
O
OH
O
O
Scheme 4 Synthesis of mammea A/AA cyclo D (220)