Biomedical Engineering Reference
In-Depth Information
OTBDPS
HO
( )
n
O
C
12
H
25
404a
(
n
= 2)
404b
(
n
= 4)
O
1. Re
2
O
7
, (CF
3
CO)
2
O, THF, rt, 1 h
2.
404
, CH
2
Cl
2
, (CF
3
CO)
2
O, 0°C to rt
OR
HO
( )
n
O
O
O
C
12
H
25
O
405a
(
n
= 2, R = TBDPS, 49%)
405b
(
n
= 4, R = H, 29%)
1 or 2 steps
OH
HO
( )
n
O
O
O
C
12
H
25
Rollidecin C (
n
= 2,
406a
)
Rollidecin D (
n
= 4,
406b
)
O
SCHEME 9.71
Synthesis of rollidecins C (
406a
) and D (
406b
) by Keinan and coworkers.
HO
OTBDPS
OTBDPS
OTBDPS
O
MeO
MeO
MeO
O
O
O
DMP, CH
2
Cl
2
air, rt
O
OH
HO
HO
82%
C
8
H
15
C
8
H
15
C
8
H
15
OPiv
OPiv
OPiv
409
410
(Proven intermediate)
411
DMP, 16 h
O
OH
2
TBSO
OTBDPS
OTBDPS
O
C
5
H
9
O
MeO
MeO
O
O
O
OH
O
OH
steps
O
O
X
O
C
8
H
15
C
8
H
15
C
8
H
15
OTES
PivO
PivO
415
413
(X = H, OH)
414
(X = O)
412
TEMPO
68%
O
O
HO
O
O
O
O
O
OH
O
O
O
O
O
O
CO
2
H
CO
2
H
CP-263114
407
CP-225917
408
SCHEME 9.72
Synthesis of the CP molecules by Nicolaou and coworkers.
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