H O

O O OH O R2
-H2O
C C + C C C
C R2 C C C
R1 R1 R3 R1
H R2 R3 R3
H
4
1 2 3

OH O OH O OH O OH O

R2 R1 R2 R1 R2 R1 R2
R1

syn / erythro anti / threo

R2
OM O
R3 H
M
C C + R1 C H O

H H R1 O
R2
9 R3
10

R2 OH O
H M syn /
O
erythro
H R1 R2
O
R1
R3
R 3 11
H H
OH O OH
H
HO O
2 H3C C CH2 C
CH2 C CH3

H H H3C O
H
 R R'
R R'

R' R'
[M] 3
'
2 R
5
R R'

[M] [M]
6

R' R R R
R' R
1
3 [M]

O
PhCH2O PhCH2O

MCPBA
O

RO OH
O O
_ _
|O| O |O|
O O
O
HO C C C C R'
C C

R R' R R' HO R
-
HO