OMe
OMe
MeO
RO
OR
OR
HO
HO
OH
HO
OH
MeO
OMe
BBr
3
CH
2 Cl
2
OMe
MeO
CHO
TsOH
TCE, 100°C
15%
Cl
2 CHOMe, AlCl
3
DCM, 0°C
NaBH
4 , THF/MeOH
98%
HO
OH
OH
OH
OH
HO
HO
(+)-P-67
(-)-M-67
O
ClO
2 S
1) DMAP, Et
3 N, DCM
68a
68b
O
O
2 S
R =
KOH
THF/MeOH
(±)- 66
MeO
OMe
OMe
2) Separation
KOH
THF/MeOH
81%
63
OMe
MeO
64
benzenediazonium2-carboxylate,
1,2epoxypropane, reflux
67%
97%
93%
RO
OR
OR
RO
RO
OR
OR
RO
RO
OMe
MeO
CH
2 OH
65
97%
OH
OH
HO
(±)- 67
HO
OH
OH
Scheme 13
Synthesis and resolution of (Æ)-67
168
Y. Han and C.-F. Chen