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Intermolecular oxidative enolate heterocoupling
被引:165
作者
:
Baran, Phil S.
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, Phil S.
[
1
]
DeMartino, Michael P.
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
DeMartino, Michael P.
[
1
]
机构
:
[1]
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2006年
/ 45卷
/ 42期
关键词
:
C-C coupling;
enolates;
lignans;
synthetic methods;
total synthesis;
D O I
:
10.1002/anie.200603024
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) No priming necessary: The intermolecular oxidative heterocoupling of imides and oxindoles to esters, ketones, and lactones is shown for the first time to be synthetically viable. Strategic use of the initial oxidation state of the reactants allows for the excision of prefunctionalization steps (halogenation, enol-silane formation) and allows for the concise synthesis of unsymmetrical lignans, such as (-)-bursehernin (1). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7083 / 7086
页数:4
相关论文
共 27 条
[1]
[Anonymous], 2005, ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANGE.200461864
[2]
BALKOVEC JM, 2001, Patent No. 29687
[3]
Enantioselective total synthesis of avrainvillamide and the stephacidins
Baran, Phil S.
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, Phil S.
Hafensteiner, Benjamin D.
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
Hafensteiner, Benjamin D.
Ambhaikar, Narendra B.
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
Ambhaikar, Narendra B.
Guerrero, Carlos A.
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
Guerrero, Carlos A.
Gallagher, John D.
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
Gallagher, John D.
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006,
128
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-
8693
[4]
Total synthesis of avrainvillamide (CJ-17,665) and stephacidin B
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
Guerrero, CA
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
Guerrero, CA
Hafensteiner, BD
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
Hafensteiner, BD
Ambhaikar, NB
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
Ambhaikar, NB
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005,
44
(25)
: 3892
-
3895
[5]
Short, enantioselective total synthesis of Stephacidin A
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
Guerrero, CA
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
Guerrero, CA
Ambhaikar, NB
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
Ambhaikar, NB
Hafensteiner, BD
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
Hafensteiner, BD
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005,
44
(04)
: 606
-
609
[6]
Direct coupling of indoles with carbonyl compounds: Short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families
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,
2004,
126
(24)
: 7450
-
7451
[7]
BARAN PS, 2005, ANGEW CHEM, V117, P615
[8]
BARAN PS, 2005, ANGEW CHEM, V117, P3960
[9]
OXIDATIVE COUPLING OF CARBOXYLIC-ACID DIANIONS - THE TOTAL SYNTHESIS OF (+/-)-HINOKININ AND (+/-)-FOMENTARIC ACID
BELLETIRE, JL
论文数:
0
引用数:
0
h-index:
0
BELLETIRE, JL
FRY, DF
论文数:
0
引用数:
0
h-index:
0
FRY, DF
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1987,
52
(12)
: 2549
-
2555
[10]
OXIDATION BY METAL-SALTS .12. NOVEL ONE-STEP SYNTHESIS OF 1,4 DIKETONES
DESSAU, RM
论文数:
0
引用数:
0
h-index:
0
机构:
MOBIL RES & DEV CORP,CENT RES DIV,PRINCETON,NJ 08540
MOBIL RES & DEV CORP,CENT RES DIV,PRINCETON,NJ 08540
DESSAU, RM
HEIBA, EI
论文数:
0
引用数:
0
h-index:
0
机构:
MOBIL RES & DEV CORP,CENT RES DIV,PRINCETON,NJ 08540
MOBIL RES & DEV CORP,CENT RES DIV,PRINCETON,NJ 08540
HEIBA, EI
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1974,
39
(23)
: 3457
-
3459
←
1
2
3
→
共 27 条
[1]
[Anonymous], 2005, ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANGE.200461864
[2]
BALKOVEC JM, 2001, Patent No. 29687
[3]
Enantioselective total synthesis of avrainvillamide and the stephacidins
Baran, Phil S.
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, Phil S.
Hafensteiner, Benjamin D.
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
Hafensteiner, Benjamin D.
Ambhaikar, Narendra B.
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
Ambhaikar, Narendra B.
Guerrero, Carlos A.
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
Guerrero, Carlos A.
Gallagher, John D.
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
Gallagher, John D.
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006,
128
(26)
: 8678
-
8693
[4]
Total synthesis of avrainvillamide (CJ-17,665) and stephacidin B
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
Guerrero, CA
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
Guerrero, CA
Hafensteiner, BD
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
Hafensteiner, BD
Ambhaikar, NB
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
Ambhaikar, NB
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005,
44
(25)
: 3892
-
3895
[5]
Short, enantioselective total synthesis of Stephacidin A
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
Guerrero, CA
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
Guerrero, CA
Ambhaikar, NB
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
Ambhaikar, NB
Hafensteiner, BD
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
Hafensteiner, BD
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005,
44
(04)
: 606
-
609
[6]
Direct coupling of indoles with carbonyl compounds: Short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families
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,
2004,
126
(24)
: 7450
-
7451
[7]
BARAN PS, 2005, ANGEW CHEM, V117, P615
[8]
BARAN PS, 2005, ANGEW CHEM, V117, P3960
[9]
OXIDATIVE COUPLING OF CARBOXYLIC-ACID DIANIONS - THE TOTAL SYNTHESIS OF (+/-)-HINOKININ AND (+/-)-FOMENTARIC ACID
BELLETIRE, JL
论文数:
0
引用数:
0
h-index:
0
BELLETIRE, JL
FRY, DF
论文数:
0
引用数:
0
h-index:
0
FRY, DF
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1987,
52
(12)
: 2549
-
2555
[10]
OXIDATION BY METAL-SALTS .12. NOVEL ONE-STEP SYNTHESIS OF 1,4 DIKETONES
DESSAU, RM
论文数:
0
引用数:
0
h-index:
0
机构:
MOBIL RES & DEV CORP,CENT RES DIV,PRINCETON,NJ 08540
MOBIL RES & DEV CORP,CENT RES DIV,PRINCETON,NJ 08540
DESSAU, RM
HEIBA, EI
论文数:
0
引用数:
0
h-index:
0
机构:
MOBIL RES & DEV CORP,CENT RES DIV,PRINCETON,NJ 08540
MOBIL RES & DEV CORP,CENT RES DIV,PRINCETON,NJ 08540
HEIBA, EI
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1974,
39
(23)
: 3457
-
3459
←
1
2
3
→