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Synthetic studies on polyoxypeptins:: stereoselective synthesis of (2S,3R)-3-hydroxy-3-methylproline using SmI2-mediated cyclization
被引:21
作者
:
Makino, K
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Makino, K
[
1
]
Kondoh, A
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Kondoh, A
[
1
]
Hamada, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Hamada, Y
[
1
]
机构
:
[1]
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
来源
:
TETRAHEDRON LETTERS
|
2002年
/ 43卷
/ 26期
关键词
:
(2S;
3R)-3-hydroxy-3-methylproline;
samarium iodide;
Barbier-type reaction;
D O I
:
10.1016/S0040-4039(02)00833-X
中图分类号
:
O62 [有机化学];
学科分类号
:
070303 ;
081704 ;
摘要
:
Stereoselective synthesis of (2S,3R)-3-hydroxy-3-methylproline (3), a component of polyoxypeptins. has been achieved by use of SmI2-mediated diastereoselective cyclization reaction as a key step. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4695 / 4698
页数:4
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A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES
DESS, DB
论文数:
0
引用数:
0
h-index:
0
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VANDERBILT UNIV,DEPT CHEM,NASHVILLE,TN 37240
DESS, DB
MARTIN, JC
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0
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0
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0
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VANDERBILT UNIV,DEPT CHEM,NASHVILLE,TN 37240
MARTIN, JC
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1991,
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7287
[2]
READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES
DESS, DB
论文数:
0
引用数:
0
h-index:
0
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UNIV ILLINOIS,ROGER ADAMS LAB,DEPT CHEM,URBANA,IL 61801
UNIV ILLINOIS,ROGER ADAMS LAB,DEPT CHEM,URBANA,IL 61801
DESS, DB
MARTIN, JC
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0
引用数:
0
h-index:
0
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UNIV ILLINOIS,ROGER ADAMS LAB,DEPT CHEM,URBANA,IL 61801
UNIV ILLINOIS,ROGER ADAMS LAB,DEPT CHEM,URBANA,IL 61801
MARTIN, JC
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1983,
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4156
[3]
AN IMPROVED PROCEDURE FOR THE PREPARATION OF THE DESS-MARTIN PERIODINANE
IRELAND, RE
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0
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0
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IRELAND, RE
LIU, LB
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0
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0
LIU, LB
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1993,
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2899
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KAWATSURA M, 1995, SYNLETT, P729
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SAMARIUM(II) IODIDE PROMOTED INTERMOLECULAR KETONE OLEFIN COUPLINGS CHELATION-CONTROLLED BY ALPHA-HYDROXYL GROUPS
KAWATSURA, M
论文数:
0
引用数:
0
h-index:
0
机构:
HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN
HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN
KAWATSURA, M
MATSUDA, F
论文数:
0
引用数:
0
h-index:
0
机构:
HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN
HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN
MATSUDA, F
SHIRAHAMA, H
论文数:
0
引用数:
0
h-index:
0
机构:
HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN
HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN
SHIRAHAMA, H
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1994,
59
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: 6900
-
6901
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KITO M, 1993, SYNLETT, P158
[7]
Coupling of organic halides with carbonyl compounds promoted by SmI2, the Kagan reagent
Krief, A
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0
引用数:
0
h-index:
0
机构:
Fac Univ Notre Dame Paix, Lab Chim Organ Synthese, Dept Chim, B-5000 Namur, Belgium
Fac Univ Notre Dame Paix, Lab Chim Organ Synthese, Dept Chim, B-5000 Namur, Belgium
Krief, A
Laval, AM
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0
引用数:
0
h-index:
0
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Fac Univ Notre Dame Paix, Lab Chim Organ Synthese, Dept Chim, B-5000 Namur, Belgium
Fac Univ Notre Dame Paix, Lab Chim Organ Synthese, Dept Chim, B-5000 Namur, Belgium
Laval, AM
[J].
CHEMICAL REVIEWS,
1999,
99
(03)
: 745
-
777
[8]
A practical synthesis of the lipophilic side chain of the polyoxypeptins
Lorca, M
论文数:
0
引用数:
0
h-index:
0
机构:
Florida State Univ, Dept Chem, Tallahassee, FL 32306 USA
Florida State Univ, Dept Chem, Tallahassee, FL 32306 USA
Lorca, M
Kurosu, M
论文数:
0
引用数:
0
h-index:
0
机构:
Florida State Univ, Dept Chem, Tallahassee, FL 32306 USA
Florida State Univ, Dept Chem, Tallahassee, FL 32306 USA
Kurosu, M
[J].
TETRAHEDRON LETTERS,
2001,
42
(13)
: 2431
-
2434
[9]
Efficient enantioselective synthesis of (2R,3R)- and (2S,3S)-3-hydroxyleucines and their diastereomers through dynamic kinetic resolution
Makino, K
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Makino, K
Okamoto, N
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Okamoto, N
Hara, O
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Hara, O
Hamada, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Hamada, Y
[J].
TETRAHEDRON-ASYMMETRY,
2001,
12
(12)
: 1757
-
1762
[10]
HYDROXYL-DIRECTED CARBON-CARBON BOND FORMATION REACTIONS MEDIATED BY SAMARIUM(II) IODIDE
MATSUDA, F
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Science, Hokkaido University
MATSUDA, F
[J].
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN,
1995,
53
(11)
: 987
-
998
←
1
2
→
共 19 条
[1]
A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES
DESS, DB
论文数:
0
引用数:
0
h-index:
0
机构:
VANDERBILT UNIV,DEPT CHEM,NASHVILLE,TN 37240
DESS, DB
MARTIN, JC
论文数:
0
引用数:
0
h-index:
0
机构:
VANDERBILT UNIV,DEPT CHEM,NASHVILLE,TN 37240
MARTIN, JC
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1991,
113
(19)
: 7277
-
7287
[2]
READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES
DESS, DB
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ILLINOIS,ROGER ADAMS LAB,DEPT CHEM,URBANA,IL 61801
UNIV ILLINOIS,ROGER ADAMS LAB,DEPT CHEM,URBANA,IL 61801
DESS, DB
MARTIN, JC
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ILLINOIS,ROGER ADAMS LAB,DEPT CHEM,URBANA,IL 61801
UNIV ILLINOIS,ROGER ADAMS LAB,DEPT CHEM,URBANA,IL 61801
MARTIN, JC
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1983,
48
(22)
: 4155
-
4156
[3]
AN IMPROVED PROCEDURE FOR THE PREPARATION OF THE DESS-MARTIN PERIODINANE
IRELAND, RE
论文数:
0
引用数:
0
h-index:
0
IRELAND, RE
LIU, LB
论文数:
0
引用数:
0
h-index:
0
LIU, LB
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1993,
58
(10)
: 2899
-
2899
[4]
KAWATSURA M, 1995, SYNLETT, P729
[5]
SAMARIUM(II) IODIDE PROMOTED INTERMOLECULAR KETONE OLEFIN COUPLINGS CHELATION-CONTROLLED BY ALPHA-HYDROXYL GROUPS
KAWATSURA, M
论文数:
0
引用数:
0
h-index:
0
机构:
HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN
HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN
KAWATSURA, M
MATSUDA, F
论文数:
0
引用数:
0
h-index:
0
机构:
HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN
HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN
MATSUDA, F
SHIRAHAMA, H
论文数:
0
引用数:
0
h-index:
0
机构:
HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN
HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN
SHIRAHAMA, H
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1994,
59
(23)
: 6900
-
6901
[6]
KITO M, 1993, SYNLETT, P158
[7]
Coupling of organic halides with carbonyl compounds promoted by SmI2, the Kagan reagent
Krief, A
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Univ Notre Dame Paix, Lab Chim Organ Synthese, Dept Chim, B-5000 Namur, Belgium
Fac Univ Notre Dame Paix, Lab Chim Organ Synthese, Dept Chim, B-5000 Namur, Belgium
Krief, A
Laval, AM
论文数:
0
引用数:
0
h-index:
0
机构:
Fac Univ Notre Dame Paix, Lab Chim Organ Synthese, Dept Chim, B-5000 Namur, Belgium
Fac Univ Notre Dame Paix, Lab Chim Organ Synthese, Dept Chim, B-5000 Namur, Belgium
Laval, AM
[J].
CHEMICAL REVIEWS,
1999,
99
(03)
: 745
-
777
[8]
A practical synthesis of the lipophilic side chain of the polyoxypeptins
Lorca, M
论文数:
0
引用数:
0
h-index:
0
机构:
Florida State Univ, Dept Chem, Tallahassee, FL 32306 USA
Florida State Univ, Dept Chem, Tallahassee, FL 32306 USA
Lorca, M
Kurosu, M
论文数:
0
引用数:
0
h-index:
0
机构:
Florida State Univ, Dept Chem, Tallahassee, FL 32306 USA
Florida State Univ, Dept Chem, Tallahassee, FL 32306 USA
Kurosu, M
[J].
TETRAHEDRON LETTERS,
2001,
42
(13)
: 2431
-
2434
[9]
Efficient enantioselective synthesis of (2R,3R)- and (2S,3S)-3-hydroxyleucines and their diastereomers through dynamic kinetic resolution
Makino, K
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Makino, K
Okamoto, N
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Okamoto, N
Hara, O
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Hara, O
Hamada, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Hamada, Y
[J].
TETRAHEDRON-ASYMMETRY,
2001,
12
(12)
: 1757
-
1762
[10]
HYDROXYL-DIRECTED CARBON-CARBON BOND FORMATION REACTIONS MEDIATED BY SAMARIUM(II) IODIDE
MATSUDA, F
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Science, Hokkaido University
MATSUDA, F
[J].
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN,
1995,
53
(11)
: 987
-
998
←
1
2
→