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Total synthesis of (±)-welwitindolinone A isonitrile
被引:117
作者
:
Reisman, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06520 USA
Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06520 USA
Reisman, SE
[
1
]
Ready, JM
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06520 USA
Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06520 USA
Ready, JM
[
1
]
Hasuoka, A
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06520 USA
Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06520 USA
Hasuoka, A
[
1
]
Smith, CJ
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06520 USA
Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06520 USA
Smith, CJ
[
1
]
Wood, JL
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06520 USA
Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06520 USA
Wood, JL
[
1
]
机构
:
[1]
Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06520 USA
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2006年
/ 128卷
/ 05期
关键词
:
D O I
:
10.1021/ja057640s
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
A highly stereoselective total synthesis of the alkaloid natural product welwitindolinone A isonitrile has been completed. The synthesis utilizes a chloronium ion mediated semi-pinacol rearrangement to simultaneously install the C10 quaternary center and neopentyl chlorine and a novel anionic cyclization to construct the spiro-oxindole with complete stereocontrol. Copyright © 2006 American Chemical Society.
引用
收藏
页码:1448 / 1449
页数:2
相关论文
共 13 条
[1]
Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G
Baran, PS
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Baran, PS
Richter, JM
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Richter, JM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(44)
: 15394
-
15396
[2]
REDUCTIVE FORMYLATION OF OXIMES - AN APPROACH TO THE SYNTHESIS OF VINYL ISONITRILES
BARTON, DHR
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV STIRLING,DEPT CHEM,STIRLING FK9 4LA,SCOTLAND
BARTON, DHR
BOWLES, T
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV STIRLING,DEPT CHEM,STIRLING FK9 4LA,SCOTLAND
BOWLES, T
HUSINEC, S
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV STIRLING,DEPT CHEM,STIRLING FK9 4LA,SCOTLAND
HUSINEC, S
FORBES, JE
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV STIRLING,DEPT CHEM,STIRLING FK9 4LA,SCOTLAND
FORBES, JE
LLOBERA, A
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV STIRLING,DEPT CHEM,STIRLING FK9 4LA,SCOTLAND
LLOBERA, A
PORTER, AEA
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV STIRLING,DEPT CHEM,STIRLING FK9 4LA,SCOTLAND
PORTER, AEA
ZARD, SZ
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV STIRLING,DEPT CHEM,STIRLING FK9 4LA,SCOTLAND
ZARD, SZ
[J].
TETRAHEDRON LETTERS,
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3346
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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,
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[4]
DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE
EVANS, DA
论文数:
0
引用数:
0
h-index:
0
EVANS, DA
CHAPMAN, KT
论文数:
0
引用数:
0
h-index:
0
CHAPMAN, KT
CARREIRA, EM
论文数:
0
引用数:
0
h-index:
0
CARREIRA, EM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1988,
110
(11)
: 3560
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3578
[5]
ALPHA-METALATED ISOCYANIDES IN ORGANIC SYNTHESIS
HOPPE, D
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV GOTTINGEN, ORG CHEM INST, WINDAUS WEG 2, 34 GOTTINGEN, WEST GERMANY
UNIV GOTTINGEN, ORG CHEM INST, WINDAUS WEG 2, 34 GOTTINGEN, WEST GERMANY
HOPPE, D
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
1974,
13
(12)
: 789
-
804
[6]
Oxidized welwitindolinones from terrestrial Fischerella spp.
Jimenez, JI
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Jimenez, JI
Huber, U
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Huber, U
Moore, RE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Moore, RE
Patterson, GML
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Patterson, GML
[J].
JOURNAL OF NATURAL PRODUCTS,
1999,
62
(04):
: 569
-
572
[7]
Reductive cleavage of N-O bonds in hydroxylamines and hydroxamic acid derivatives using samarium diiodide
Keck, GE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
Keck, GE
Wager, TT
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
Wager, TT
McHardy, SF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
McHardy, SF
[J].
TETRAHEDRON,
1999,
55
(40)
: 11755
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11772
[8]
SULFURANES .3. REAGENT FOR DEHYDRATION OF ALCOHOLS
MARTIN, JC
论文数:
0
引用数:
0
h-index:
0
MARTIN, JC
ARHART, RJ
论文数:
0
引用数:
0
h-index:
0
ARHART, RJ
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1971,
93
(17)
: 4327
-
&
[9]
CeCl3/NaClO:: a safe and efficient reagent for the allylic chlorination of terminal olefins
Moreno-Dorado, FJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Moreno-Dorado, FJ
Guerra, FM
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Guerra, FM
Manzano, FL
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Manzano, FL
Aladro, FJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Aladro, FJ
Jorge, ZD
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Jorge, ZD
Massanet, GM
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Massanet, GM
[J].
TETRAHEDRON LETTERS,
2003,
44
(35)
: 6691
-
6693
[10]
IMPROVED PROTOCOLS FOR THE SELECTIVE DEPROTECTION OF TRIALKYLSILYL ETHERS USING FLUOROSILICIC ACID
PILCHER, AS
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV MARYLAND,DEPT CHEM & BIOCHEM,COLL PK,MD 20742
UNIV MARYLAND,DEPT CHEM & BIOCHEM,COLL PK,MD 20742
PILCHER, AS
DESHONG, P
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV MARYLAND,DEPT CHEM & BIOCHEM,COLL PK,MD 20742
UNIV MARYLAND,DEPT CHEM & BIOCHEM,COLL PK,MD 20742
DESHONG, P
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1993,
58
(19)
: 5130
-
5134
←
1
2
→
共 13 条
[1]
Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G
Baran, PS
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Baran, PS
Richter, JM
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Richter, JM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(44)
: 15394
-
15396
[2]
REDUCTIVE FORMYLATION OF OXIMES - AN APPROACH TO THE SYNTHESIS OF VINYL ISONITRILES
BARTON, DHR
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV STIRLING,DEPT CHEM,STIRLING FK9 4LA,SCOTLAND
BARTON, DHR
BOWLES, T
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV STIRLING,DEPT CHEM,STIRLING FK9 4LA,SCOTLAND
BOWLES, T
HUSINEC, S
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV STIRLING,DEPT CHEM,STIRLING FK9 4LA,SCOTLAND
HUSINEC, S
FORBES, JE
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV STIRLING,DEPT CHEM,STIRLING FK9 4LA,SCOTLAND
FORBES, JE
LLOBERA, A
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV STIRLING,DEPT CHEM,STIRLING FK9 4LA,SCOTLAND
LLOBERA, A
PORTER, AEA
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV STIRLING,DEPT CHEM,STIRLING FK9 4LA,SCOTLAND
PORTER, AEA
ZARD, SZ
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV STIRLING,DEPT CHEM,STIRLING FK9 4LA,SCOTLAND
ZARD, SZ
[J].
TETRAHEDRON LETTERS,
1988,
29
(27)
: 3343
-
3346
[3]
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
[4]
DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE
EVANS, DA
论文数:
0
引用数:
0
h-index:
0
EVANS, DA
CHAPMAN, KT
论文数:
0
引用数:
0
h-index:
0
CHAPMAN, KT
CARREIRA, EM
论文数:
0
引用数:
0
h-index:
0
CARREIRA, EM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1988,
110
(11)
: 3560
-
3578
[5]
ALPHA-METALATED ISOCYANIDES IN ORGANIC SYNTHESIS
HOPPE, D
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV GOTTINGEN, ORG CHEM INST, WINDAUS WEG 2, 34 GOTTINGEN, WEST GERMANY
UNIV GOTTINGEN, ORG CHEM INST, WINDAUS WEG 2, 34 GOTTINGEN, WEST GERMANY
HOPPE, D
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
1974,
13
(12)
: 789
-
804
[6]
Oxidized welwitindolinones from terrestrial Fischerella spp.
Jimenez, JI
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Jimenez, JI
Huber, U
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Huber, U
Moore, RE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Moore, RE
Patterson, GML
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
Patterson, GML
[J].
JOURNAL OF NATURAL PRODUCTS,
1999,
62
(04):
: 569
-
572
[7]
Reductive cleavage of N-O bonds in hydroxylamines and hydroxamic acid derivatives using samarium diiodide
Keck, GE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
Keck, GE
Wager, TT
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
Wager, TT
McHardy, SF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
McHardy, SF
[J].
TETRAHEDRON,
1999,
55
(40)
: 11755
-
11772
[8]
SULFURANES .3. REAGENT FOR DEHYDRATION OF ALCOHOLS
MARTIN, JC
论文数:
0
引用数:
0
h-index:
0
MARTIN, JC
ARHART, RJ
论文数:
0
引用数:
0
h-index:
0
ARHART, RJ
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1971,
93
(17)
: 4327
-
&
[9]
CeCl3/NaClO:: a safe and efficient reagent for the allylic chlorination of terminal olefins
Moreno-Dorado, FJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Moreno-Dorado, FJ
Guerra, FM
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Guerra, FM
Manzano, FL
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Manzano, FL
Aladro, FJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Aladro, FJ
Jorge, ZD
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Jorge, ZD
Massanet, GM
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
Massanet, GM
[J].
TETRAHEDRON LETTERS,
2003,
44
(35)
: 6691
-
6693
[10]
IMPROVED PROTOCOLS FOR THE SELECTIVE DEPROTECTION OF TRIALKYLSILYL ETHERS USING FLUOROSILICIC ACID
PILCHER, AS
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV MARYLAND,DEPT CHEM & BIOCHEM,COLL PK,MD 20742
UNIV MARYLAND,DEPT CHEM & BIOCHEM,COLL PK,MD 20742
PILCHER, AS
DESHONG, P
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV MARYLAND,DEPT CHEM & BIOCHEM,COLL PK,MD 20742
UNIV MARYLAND,DEPT CHEM & BIOCHEM,COLL PK,MD 20742
DESHONG, P
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1993,
58
(19)
: 5130
-
5134
←
1
2
→