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OBn
O
CO
2
t
Bu
Me
OBn
CuOAc
CO
2
t
-Bu
O
O
OH
N
H
Me
DBU (
1
)
N
H
NHNs
+
toluene
90%
N
CO
2
Bn
CO
2
Bn
HO
Ns
HO
N
N
170
Boc
Me
Boc
Me
171
169
Me
OH
O
CO
2
H
Me
O
H
HN
O
O
HO
N
H
Me
NHMe
Me
ustiloxin D (
172
)
Scheme 7.38
Synthesis of ustiloxin D (172)
Table 7.1
Aziridine ring opening reaction with phenols in the presence of TBD (7)
Me
OTBS
N
Ns
X
X
O
Me
174
O
NH
OH
method A or B
NHNs
173
175
Yield of
175
(%)
X
method A
method B
H
39
78
Br
22
73
Me
31
71
CN
—
84
CHO
—
69
method A
: Ar-OH (2.2 equiv.), DBU (
) (2.2 equiv.), CuOAc (2.5mol%), toluene.
1
method B
: Ar-OH (2 equiv.), TBD (
) (2 equiv.), toluene.
7
