Biomedical Engineering Reference
In-Depth Information
O
O
R
2
R
2
X
R
1
H
R
1
NH
2
X = I, Br
Nicolaou and coworkers (2002)
CuTC, Rb
2
CO
3
DMA, 90°C
(90%)
(E/Z
10:1)
CuTC, Rb
2
CO
3
DMA, 90°C
(57%)
(E/Z
2.5:1)
Me
H
N
OH
Me
O
O
OH
O
O
H
OH
O
O
H
H
O
Panek and coworkers (2005)
CuTC, Rb
2
CO
3
,
L6
DMA, 58°C
(40%)
(
E/Z
8:1)
Me
Salicylihalamide A : (
E
)
Salicylihalamide B : (
Z
)
Fürstner and coworkers (2001)
Apicularen A
OH
CuTC,
L11
, K
2
CO
3
DMA, 50°C
(45%)
(
E/Z
7:1)
CuTC,
L11
, K
2
CO
3
DMA, 50°C
(44%)
N
N
Ph
OH
CuI,
L15
Cs
2
CO
3
dioxane
reflux
(82%)
O
O
N
OH
N
OMe
OH
O
OH
O
O
OMe
O
O
NMe
O
Oximidine II
Porco and coworkers (2003)
Oximidine III
Porco and coworkers (2004)
-Clausenamide
Wang and coworkers (2007)
(+)-
ξ
CuI,
L15
, Cs
2
CO
3
dioxane, 80°C
(60-61%)
O
R
1
MeO
O
N
Me
MeHN
O
NH
NH
Me
O
Me
Me
OH
O
Me
HO
R
2
CuI,
L11
, Cs
2
CO
3
DMF, 23°C
(44%)
H
O
O
Me
O
NH
2
Palmerolide A
Nicolaou, Chen and coworkers (2007)
Abyssenine
B: R
1
= H; R
2
= CH(Me)Et
Mucronine E: R
1
= OMe; R
2
= CH
2
CH(Me)
2
Ma and coworkers (2007)
CuI,
L11
, Cs
2
CO
3
THF, 70°C
(67%)
O
Me
OMe
OMe
O
H
N
O
H
N
MeO
Me
Me
Crocacin D
Dias and coworkers (2005)
SCHEME 3.28
Selected examples of enamide natural products synthesized by copper
amidation.
In the first total synthesis of oximidines II [68] and III [69] published by Porco
and Wang in 2003 and Porco and coworkers in 2004, respectively, the construction of
the unsaturated enamide side chain was realized using a copper(I)-mediated cross-
coupling of a vinyl iodide with an oxime amide in the late stage of each synthesis. In
2007, Wang and coworkers developed a very practical and efficient
N
-vinylation of
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