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For an early example of 1,5-radical translocation from a protecting group, see
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For examples of C-H bond oxidation α to oxygen of alcohol derivatives, see: (a) Lewin, A. H.; Dinwoodie, A. H.; Cohen, T. Tetrahedron 1966, 22, 1527-1537.
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-
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37249040724
-
-
Synthesis of 3-hydroxyproline derivative 6 is described in the Supporting Information.
-
Synthesis of 3-hydroxyproline derivative 6 is described in the Supporting Information.
-
-
-
-
43
-
-
37249092736
-
-
Attempted cleavage of the TBS group under several other conditions (TBAF, HF/pyridine, or MeOH in HCl) led to significant decomposition
-
Attempted cleavage of the TBS group under several other conditions (TBAF, HF/pyridine, or MeOH in HCl) led to significant decomposition.
-
-
-
-
44
-
-
0000079538
-
-
For pioneering studies of the use of (bromomethyl)dimethylsiloxy ethers in free radical chain reactions, see: a
-
For pioneering studies of the use of (bromomethyl)dimethylsiloxy ethers in free radical chain reactions, see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300.
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Nishiyama, H.1
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Itoh, K.4
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46
-
-
37249000089
-
-
The synthesis of α-bromomethylsilyl 13 is described in the Supporting Information.
-
The synthesis of α-bromomethylsilyl 13 is described in the Supporting Information.
-
-
-
-
47
-
-
37249092236
-
-
In an early calibration experiment, the reaction of iodoacetal i with tributyltin hydride, AIBN, and TEMPO in benzene at 85°C resulted only in substitution at the acetal substituent to provide TEMPO adduct ii. This result showed that the primary radical derived from i was trapped with TEMPO faster than it underwent 1,5-hydrogen atom transfer
-
In an early calibration experiment, the reaction of iodoacetal i with tributyltin hydride, AIBN, and TEMPO in benzene at 85°C resulted only in substitution at the acetal substituent to provide TEMPO adduct ii. This result showed that the primary radical derived from i was trapped with TEMPO faster than it underwent 1,5-hydrogen atom transfer.
-
-
-
-
48
-
-
37249068715
-
-
These modifications were developed during contemporaneous studies of the oxidation of an analogue of 12 having an isopropylidene substituent at C3
-
These modifications were developed during contemporaneous studies of the oxidation of an analogue of 12 having an isopropylidene substituent at C3.
-
-
-
-
49
-
-
37249086403
-
-
The relative configuration of these products was determined by NOESY NMR experiments; see the Supporting Information for details
-
The relative configuration of these products was determined by NOESY NMR experiments; see the Supporting Information for details.
-
-
-
-
50
-
-
37249070552
-
-
2 could be reduced to 7 equiv; however, yields of angular oxidation were maximized by using an equal excess of the silane.
-
2 could be reduced to 7 equiv; however, yields of angular oxidation were maximized by using an equal excess of the silane.
-
-
-
-
51
-
-
37249085327
-
-
The construction of epidithiodioxopiperazines from dioxopiperazines that contain two leaving groups by ZnCl2-promoted reaction of H 2S has been reported; see refs 4d, 4e, 4k, and 41
-
2S has been reported; see refs 4d, 4e, 4k, and 41.
-
-
-
-
52
-
-
37249002054
-
-
More conventional conditions for removing the acetate group were not compatible with the disulfide bridge
-
More conventional conditions for removing the acetate group were not compatible with the disulfide bridge.
-
-
-
-
53
-
-
37249011563
-
-
CCDC 663428. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
-
CCDC 663428. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
-
-
-
-
54
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23744510729
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