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O
O
O
D-glucose
O
O
C
12
H
25
O
OTs
4
3
Sharpless AD
C
12
H
25
C
12
H
25
O
I
O
O
MOMO
MOMO
OH
5
6
(R,R)-salenCo(OAc)
O
O
( )
6
methyl
undecenoate
( )
6
O
H
2
O
O
O
O
7
8
6
O
O
C
12
H
25
22
17
10
( )
2
( )
6
O
( )
6
HO
HO
OH
O
O
OH
9
4-deoxyannomontacin
Scheme 10-5. Total synthesis of 4-deoxyannomonatacin by Wu et al.
segments was accomplished to afford the whole skeleton. The target was finally
afforded after diimide-based selective reductions of double and triple bonds and
deprotection of methoxymethyl (MOM) ethers.
Tonkinecin (Scheme 10-6) was an example of rare mono-THF acetogenins bear-
ing a C-5 hydroxyl group. Starting from D-xylose, the ester 10 was prepared in
OTHP
OH
AcO
CO
2
Me
C
HO
O
OHC
D-xylose
O
O
OMOM
10
O
11
I
Br
OH
I
PPh
3
Br
( )
3
( )
3
12
O
I
( )
4
O
OMOM
O
17
5
C
12
H
25
22
13
( )
9
O
HO
HO
OH
O
C
12
H
25
tonkinecin
O
MOMO
MOMO
14
Scheme 10-6. Total synthesis of tonkinecin by Wu et al.
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