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Direct synthesis of (+)-erogorgiaene through a kinetic enantiodifferentiating step
被引:67
作者
:
Davies, HML
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Davies, HML
[
1
]
Walji, AM
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Walji, AM
[
1
]
机构
:
[1]
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2005年
/ 44卷
/ 11期
关键词
:
C-H activation;
enantioselectivity;
natural products;
terpenoids;
total synthesis;
D O I
:
10.1002/anie.200462227
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) The combined approach of C-H activation and a Cope rearrangement catalyzed by a rhodium catalyst [Rh2(R-dosp) 4] (dosp = (N-dodecylbenzenesulfonyl)prolinate) is shown to be a very effective method for the construction of the three stereogenic centers (marked in red, see scheme) present in the diterpene erogorgiaene (1). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1733 / 1735
页数:3
相关论文
共 17 条
[1]
Cesati RR, 2004, J AM CHEM SOC, V126, P96
[2]
COLOMBIASIN A, 2003, ANGEW CHEM INT EDIT, V42, P1267
[3]
COLOMIASIN A, 2003, ANGEW CHEM, V115, P1305
[4]
A direct and efficient stereocontrolled synthetic route to the pseudopterosins, potent marine antiinflammatory agents
Corey, EJ
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Corey, EJ
Lazerwith, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Lazerwith, SE
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1998,
120
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: 12777
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12782
[5]
First enantiospecific total synthesis of the antitubercular marine natural product pseudopteroxazole. Revision of assigned stereochemistry
Davidson, JP
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Davidson, JP
Corey, EJ
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Corey, EJ
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2003,
125
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13489
[6]
Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion
Davies, HML
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Davies, HML
Beckwith, REJ
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Beckwith, REJ
[J].
CHEMICAL REVIEWS,
2003,
103
(08)
: 2861
-
2903
[7]
Catalytic asymmetric reactions for organic synthesis: The combined C-H activation/Cope rearrangement
Davies, HML
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Davies, HML
Jin, QH
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Jin, QH
[J].
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA,
2004,
101
(15)
: 5472
-
5475
[8]
GERLITS OO, 2004, COMMUNICATION
[9]
Total synthesis of elisabethin A: Intramolecular Diels-Alder reaction under biomimetic conditions
Heckrodt, TJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria
Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria
Heckrodt, TJ
Mulzer, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria
Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria
Mulzer, J
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2003,
125
(16)
: 4680
-
4681
[10]
THE PSEUDOPTEROSINS - ANTIINFLAMMATORY AND ANALGESIC NATURAL-PRODUCTS FROM THE SEA WHIP PSEUDOPTEROGORGIA-ELISABETHAE
LOOK, SA
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF SANTA BARBARA,DEPT BIOL SCI,SANTA BARBARA,CA 93106
LOOK, SA
FENICAL, W
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF SANTA BARBARA,DEPT BIOL SCI,SANTA BARBARA,CA 93106
FENICAL, W
JACOBS, RS
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF SANTA BARBARA,DEPT BIOL SCI,SANTA BARBARA,CA 93106
JACOBS, RS
CLARDY, J
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF SANTA BARBARA,DEPT BIOL SCI,SANTA BARBARA,CA 93106
CLARDY, J
[J].
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA,
1986,
83
(17)
: 6238
-
6240
←
1
2
→
共 17 条
[1]
Cesati RR, 2004, J AM CHEM SOC, V126, P96
[2]
COLOMBIASIN A, 2003, ANGEW CHEM INT EDIT, V42, P1267
[3]
COLOMIASIN A, 2003, ANGEW CHEM, V115, P1305
[4]
A direct and efficient stereocontrolled synthetic route to the pseudopterosins, potent marine antiinflammatory agents
Corey, EJ
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Corey, EJ
Lazerwith, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Lazerwith, SE
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1998,
120
(49)
: 12777
-
12782
[5]
First enantiospecific total synthesis of the antitubercular marine natural product pseudopteroxazole. Revision of assigned stereochemistry
Davidson, JP
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Davidson, JP
Corey, EJ
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Corey, EJ
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2003,
125
(44)
: 13486
-
13489
[6]
Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion
Davies, HML
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Davies, HML
Beckwith, REJ
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Beckwith, REJ
[J].
CHEMICAL REVIEWS,
2003,
103
(08)
: 2861
-
2903
[7]
Catalytic asymmetric reactions for organic synthesis: The combined C-H activation/Cope rearrangement
Davies, HML
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Davies, HML
Jin, QH
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Jin, QH
[J].
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA,
2004,
101
(15)
: 5472
-
5475
[8]
GERLITS OO, 2004, COMMUNICATION
[9]
Total synthesis of elisabethin A: Intramolecular Diels-Alder reaction under biomimetic conditions
Heckrodt, TJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria
Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria
Heckrodt, TJ
Mulzer, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria
Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria
Mulzer, J
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2003,
125
(16)
: 4680
-
4681
[10]
THE PSEUDOPTEROSINS - ANTIINFLAMMATORY AND ANALGESIC NATURAL-PRODUCTS FROM THE SEA WHIP PSEUDOPTEROGORGIA-ELISABETHAE
LOOK, SA
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF SANTA BARBARA,DEPT BIOL SCI,SANTA BARBARA,CA 93106
LOOK, SA
FENICAL, W
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF SANTA BARBARA,DEPT BIOL SCI,SANTA BARBARA,CA 93106
FENICAL, W
JACOBS, RS
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF SANTA BARBARA,DEPT BIOL SCI,SANTA BARBARA,CA 93106
JACOBS, RS
CLARDY, J
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF SANTA BARBARA,DEPT BIOL SCI,SANTA BARBARA,CA 93106
CLARDY, J
[J].
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA,
1986,
83
(17)
: 6238
-
6240
←
1
2
→