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NHTf
49
TIPSO
OPiv
NHTf
CHO
OTIPS
Zn
+
2
Ti(O
i
Pr)
4
48
47
OH
TESO
PPh
3
I
TIPSO
OPiv
( )
4
O
OTIPS
50
51
TBDMSO
O
OHC
TBDMSO
52
O
O
OHC
O
O
O
MgBr
53
C
11
H
23
OH
OH
54
O
O
C
12
H
25
( )
5
O
OH
HO
O
trans-THF
(4
R
,12
R
,15
S
,16
S
,19
R
,20
R
,34
S
)-
Muricatetrocin
(proposed structure for
Muricatetrocin B
)
OH
TBDMSO
O
TIPSO
( )
4
OPiv
OHC
(
)
5
O
OTIPS
O
55
56
OH
OH
O
54
C
12
H
25
( )
5
O
OH
HO
O
cis-THF
(4
R
,12
S
,15
S
,16
S
,19
R
,20
R
,34
S
)-
Muricatetrocin
(
Muricatetrocin A
)
Scheme 10-12. Total synthesis of muricatetrocin A and B by Baurle et al.
A similar disconnection strategy was adopted by Dixon et al. in the United Kingdom
in the synthesis of muricatetrocin C.
39,40
The retro-synthesis disconnected the
target into three parts, aldehyde 59, terminal alkyne precursor 60, and vinyl iodide
64 (Scheme 10-13). The THF-containing aldehyde 59 was prepared from com-
pound 58, an O-C rearranged product from 57. Compound 60 was synthesized
from dimethyl L-tartrate. Compound 64 was prepared with a hetero Diels-Alder
reaction. The terminal acetylene lithium derived from 60 was added to aldehyde
59, which gave a major product with erythro configuration. This erythro product
was converted into the threo product by alcohol oxidation and ketone reduction
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